Hydrochloric Acid → 4-(Methylsulfanyl)-3-(trifluoromethoxy)phenylboronic acid
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[C:4]([O:10][C:11]([F:14])([F:13])[F:12])[CH:3]=1.[B:15](OC(C)C)([O:20]C(C)C)[O:16]C(C)C.Cl>O1CCCC1>[CH3:9][S:8][C:5]1[CH:6]=[CH:7][C:2]([B:15]([OH:20])[OH:16])=[CH:3][C:4]=1[O:10][C:11]([F:14])([F:13])[F:12]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 4-bromo-1-(methylthio)-2-(trifluoromethoxy)benzene (6.63 g, 23.1 mmol) and triisopropyl borate (6.92 mL, 30.0 mmol) in tetrahydrofuran (50 mL) was added dropwise 1.6 M n-butyllithium-hexane solution (25.0 mL, 40.0 mmol) at −78° C., and the resulting mixture was stirred for 30 min. The reaction mixture was warmed to 0° C., 2 M hydrochloric acid (150 mL) was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was washed with hexane/ethyl acetate (5/1) and recrystallized from hexane/tetrahydrofuran to give the title compound (4.13 g, yield 71%) as colorless crystals.
Workup
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- washThe residue was washed with hexane/ethyl acetate (5/1)
- customrecrystallized from hexane/tetrahydrofuran
Sources & evidence
- ORD record
- ord-5d5db01571214d079710b5ed90f2b57c
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492378B2
Reaction notes
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