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

HRID 1502965ノート

反応式

HRID 1502965 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 893063732-(Trifluoromethoxy)-4-vinylbenzoic acid収率 47%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

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]E).

後処理

  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

出典と根拠

ORDレコード
ord-33ca3d74cbba43e99cdd2e225912df57
出典データセット
uspto-grants-2015_12
特許番号
US09211281B2

反応ノート

読み込み中…