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WO 2016/038627 Al 17 March 2016 (17.03.2016) P O P C T

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WO 2016/038627 Al 17 March 2016 (17.03.2016) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2016/038627 Al 17 March 2016 (17.03.2016) P O P C T (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every C07D 317/46 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (21) International Application Number: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, PCT/IN2015/000357 DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, 11 September 2015 ( 11.09.201 5) KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, OM, (25) Filing Language: English PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, (26) Publication Language: English SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: 261 1/DEL/2014 11 September 2014 ( 11.09.2014) IN (84) Designated States (unless otherwise indicated, for every kind of regional protection available): ARIPO (BW, GH, (71) Applicant: SRF LIMITED [IN/IN]; Block- C, Sector-45, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, Unicrest Building, Gurgaon 122003, Haryana (IN). TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, (72) Inventors: VARADHARAJ, Ganesan; SRF LIMITED, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, Block- C, Sector-45, Unicrest Building, Gurgaon 122003, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, Haryana (IN). POORNACHANDRAN, Ravichandran; SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, SRF LIMITED, Block- C, Sector-45, Unicrest Building, GW, KM, ML, MR, NE, SN, TD, TG). Gurgaon 122003, Haryana (IN). IYENGAR, Sarathy; SRF LIMITED, Block- C, Sector-45, Unicrest Building, Declarations under Rule 4.17 : Gurgaon 122003, Haryana (IN). PRASANNA, Kumar, — as to applicant's entitlement to apply for and be granted a Seetharaman; SRF LIMITED, Block- C, Sector-45, Uni patent (Rule 4.1 7(H)) crest Building, Gurgaon 122003, Haryana (IN). RAGURAMAN, Tiruchy, Srinivasan; SRF LIMITED, — of inventorship (Rule 4.17(iv)) Block- C, Sector-45, Unicrest Building, Gurgaon 122003, Published: Haryana (IN). GOMATHINAYAKAM, Anantharaman; Unicrest Building, Gurgaon 122003, Haryana (IN). — with international search report (Art. 21(3)) ANAND, Rajdeep; SRF LIMITED, Block- C, Sector-45, — before the expiration of the time limit for amending the Unicrest Building, Gurgaon 122003, Haryana (IN). claims and to be republished in the event of receipt of (74) Agent: SUNAINA KOUL; Lall Lahiri & Salhotra, RCY amendments (Rule 48.2(h)) House, C-235, Defence Colony, New Delhi 110024 (IN). 00 © v o (54) Title: PROCESS FOR THE PREPARATION OF HALOGENATED DERIVATIVES OF AROMATIC ETHERS (57) Abstract: The present invention relates to the process for the preparation of halogenated derivatives of aromatic ethers. PROCESS FOR T PllEPAEATiON OF HALOGEN ATED DERIVATIVES OF AROMATIC ETHERS FIELD OF THE INVENTION The present invention relates to the process for the preparation of ha oge at d derivatives of aromatic ethers Formula BACKGROUND OF THE INVENTION The halogenated derivatives. f aromatic ethers of Fomiula I p a a important role as precursors tor the preparation of medicaments and crop protection agents. Formula wherein and R' together are an oxygen atom, arid X represents a hydrogen, fluorine, chlorine, bromine or iodine. The S Patent Mo. 7,148365 describes a process for the preparation of 5-bromo- 2,2-difi o be z -l 3-di xoles b reaction of 2,2 di or benz -dioxoies with bromine in the presence of at least two Friedel-Crafts catalysts of which one is hydrogen fluoride The U.S Patent No. 4, 93,87 1 describes a process of preparation of 5-bromo-2,2- di uor ben o l ~diox les by reaction of .2,2-ditluorobeiizo- 3-diox es with bromine in the presence of carbon tetrachloride and iron powder. The processes disclosed in the listed prior art employ either toxic solvents and or lewis acids, however, the yield of mono br o derivatives obtained torn such processes is substantially low Thus, there i a need in the art to provide simple. cost-effective and industrially scalable process for the preparation of compounds of Formula I. SUMMARY OF THE INVENTION The present invention provides a process for the preparation of compounds of Formula I, comprising; a) reacting compound of Formula II with the source of bromine in the presence of hydrogen peroxide, and Formula Π wherein R and R' together are an oxygen atom, and X represents a hydrogen, fluorine, chlorine, bromine or iodine; b) isolating compound of Formula I. DETAILED DESCRIPTION OF THE INVENTION The present invention provides a process for the preparation of compounds of Formula I, comprising; a) reacting compound of Formula II with the source of bromine in the presence of hydrogen peroxide, and Formula Π wherein I d R together are an oxygen atom, and X represents a hydrogen, fluo ne chlorine, bromine or iodine; b) isolating compound of Formula The compound of Formula 0 ay be prepared b any method known in the art, for example, method known .S Patent No. 4,895,871. The bromine source may be any alkali metal bromide with mineral acid or yd ogen bromide. The alkali metal bromide may be selected from sodiu bromide, potassium bromide and caesium bromide.The step a) may take place in the presence of mineral acid. The mineral acid ma be selected from hydrochloric acid, nitric acid, f i acid, phosphoric acid, hydrofluoric acidJltiorosulfouic aeid,chkm>sulfoT« ac d or mixture thereof. he step a) may e carried out in the presence or absence of organic solvent. The step a) may be carried at a temperature of about - ft C to about 0 C for example, at about 5 C to about . The step a) may h aided by stirring the contents. The step a) may take place for about 5 minutes to about 24 hours, for example, 10 minutes to about 60 hours, for example, 30 hours to about 50 hours. The process for preparation of compound of Formula I may be carried in a continuous mode. Th compound of Formula 1 is isolated fr om step a) reaction mixture. The compound of Formula I may be isolated by filtration, layer separation, decar atio evaporation, concentration, crys a!li atio and distillation or mixture thereof While the present invention has been described in terms of its specific embodiments, certain modifications and equivalents will be apparent to those skilled in the art and are intended to be included within th scope of the present invention. EXAMPLE Example 1 Process of preparation of 5-bromo-2, 2-difluoro-l, 3-benzodioxole: A mixture of 2,2-difluoro-l, 3-benzodioxole (560 g) and Hydrogen bromide(1100 g, Assay 47%) were taken in a reaction vessel fitted with cold condenser. The reaction mixture was cooled to 10°C and 30 % Hydrogen Peroxide solution (806 g) was added slowly in lot wise. Upon completion of addition, the temperature of the reaction mixture was cautiously raised to 70°C. The organic layer was separated and washed with 20 % of sodium metabisulfite and then washed with 20% of potassium bicarbonate solution. The organic layer was dried over magnesium sulfate and filtered. The filtrate was distilled under high vacuum to obtain the title compound. Yield: 538 g W e claim: 1. A process for the preparation of compounds of Formula I, comprising; a) reacting compound of Formula II with the source of bromine in the presence of hydrogen peroxide, and Formula II Formula I wherein R and R' together are an oxygen atom, and X represents a hydrogen, fluorine, chlorine, bromine or iodine; b) isolating compound of Formula I. 2. The process of claim 1, wherein bromine source of step a) is any alkali metal bromide with mineral acid or hydrogen bromide. 3. The process of claim 2, wherein alkali metal bromide is selected from sodium bromide, potassium bromide and caesium bromide. 4. The process of claim 2, wherein mineral acid is selected from hydrochloric acid, nitric acid, sulfuric acid, phosphoric acid, hydrofluoric acid, fluoro sulfonic acid, chloro sulfonic acid or mixture thereof. 5. The process of claim 1, wherein step a) is carried at a temperature of about - 15°C to about 100°C. 6. The process of claim 1, wherein compound of Formula I is isolated by filtration, layer separation, decantation, evaporation, concentration, crystallization and distillation or mixture thereof. A . CLASSIFICATION O F SUBJECT MATTER INV. C07D317/46 ADD. According to International Patent Classification (IPC) o r t o both national classification and IPC B . FIELDS SEARCHED Minimum documentation searched (classification system followed by classification symbols) C07D Documentation searched other than minimum documentation to the extent that such documents are included in the fields searched Electronic data base consulted during the international search (name of data base and, where practicable, search terms used) EPO-Internal , CHEM ABS Data C . DOCUMENTS CONSIDERED T O B E RELEVANT Category* Citation of document, with indication, where appropriate, of the relevant passages Relevant to claim No. EP 1 595 877 Al ( LANXESS DEUTSCHLAND GMBH 1-6 [DE] ) 16 November 2005 (2005-11-16) exampl es 1, 2 J .
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