Potassium Carbonate → 2-(Trifluoromethoxy)-4-vinylbenzoic acid

HRID 1503514노트

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HRID 1503514 반응식
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:11][C:12]([F:15])([F:14])[F:13])[CH:3]=1.[CH:16]([B-](F)(F)F)=[CH2:17].[K+].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[F:13][C:12]([F:15])([F:14])[O:11][C:4]1[CH:3]=[C:2]([CH:16]=[CH2:17])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 166655724-Bromo-2-(trifluoromethoxy)benzoic acidHCID 23679353Potassium vinyltrifluoroborate

생성물 1

HCID 893063732-(Trifluoromethoxy)-4-vinylbenzoic acid수율 47%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

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온도
80 °C

실험 절차

To a stirred solution of 4-bromo-2-(trifluoromethoxy)benzoic acid (1 g, 3.67 mmol) in DMSO (20 mL) was added potassium vinyltrifluoroborate (1.47 g, 11.02 mmol) and potassium carbonate (1.52 g, 11.02 mmol). The reaction mixture was degassed with argon for 30 min Bistriphenylphosphine(diphenylphosphinoferrocene)palladium dichloride (0.13 g, 0.18 mmol) was added and the reaction mixture was heated to 80° C. for 1 h. The reaction mixture was diluted with water (100 mL), extracted with ethyl acetate (2×50 mL), washed with brine, and dried over Na2SO4. Concentration under reduced pressure furnished the crude compound which was purified by flash column chromatography to afford the product as pale yellow gummy material (0.4 g, 47%): 1H NMR (400 MHz, CDCl3) δ 8.05 (d, J=8.1 Hz, 1H), 7.44 (d, J=1.8 Hz, 1H), 7.35 (s, 1H), 6.78 (dd, J=17.4.1, 11.1 Hz, 1H), 5.92 (d, J=17.4 Hz, 1H), 5.51 (d, J=10.8 Hz, 1H); ESIMS m/z 232.97 ([M+H]+).

후처리

  1. additionwas added
  2. extractionextracted with ethyl acetate (2×50 mL)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationConcentration under reduced pressure
  6. customfurnished the crude compound which
  7. customwas purified by flash column chromatography

출처 및 근거

ORD 기록
ord-bb0b7d07f96947a5b1c1dbbc6271b41b
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212163B2

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