Water → 3-Bromo-4-(trifluoromethoxy)benzoic acid

HRID 2040531노트

반응식

HRID 2040531 반응식
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1.[Br:15]Br.O>[N+](C)([O-])=O.[Fe](Cl)(Cl)Cl>[Br:15][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:4]=1[O:3][C:2]([F:13])([F:14])[F:1])[C:8]([OH:10])=[O:9]

참가 물질

6

반응물 3

HCID 962WaterHCID 24408BromineHCID 676134-(Trifluoromethoxy)benzoic acid

생성물 1

HCID 202740913-Bromo-4-(trifluoromethoxy)benzoic acid수율 54.3%

시약·촉매·용매 2

HCID 24380Iron chloride (FeCl3)촉매HCID 6375Nitromethane용매

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온도
110 °C

실험 절차

4-(Trifluoromethoxy)benzoic acid (2 g, 9.70 mmol) and iron(III) chloride (1.574 g, 9.70 mmol) were suspended in nitromethane (20 mL). To this mixture was added bromine (0.497 mL, 9.70 mmol) at 0° C. The solution was heated under microwave irradiation at 110° C. for 2 h. The reaction mixture was added to cold water (100 mL) and extracted with ethylacetate (2×100 mL). The organic phase was washed with an aqueous solution of sodium thiosulfate pentahydrate and brine. The organic layer was concentrated and the residue was purified by HPLC to give the title compound as a white solid (1.5 g). LCMS m/z=287.0 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 7.67 (d, 1H), 8.06 (d, 1H), 8.29 (s, 1H), 13.47 (s, 1H).

후처리

  1. extractionextracted with ethylacetate (2×100 mL)
  2. washThe organic phase was washed with an aqueous solution of sodium thiosulfate pentahydrate and brine
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by HPLC

출처 및 근거

ORD 기록
ord-912725ab229247448828ea2a3f926a2c
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580841B2

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