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

HRID 1503514Notes

Reaction equation

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]

Participants

Conditions

Temperature: 80 °C

Procedure

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]+).

Workup

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

Sources & evidence

ORD record: ord-bb0b7d07f96947a5b1c1dbbc6271b41b
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212163B2

Reaction notes

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