Hydrochloric Acid → 2,4-Dimethoxybenzeneboronic acid
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][CH3:11].C([Li])CCC.C([O:20][B:21](OC(C)C)[O:22]C(C)C)(C)C.Cl>O1CCCC1.CCCCCC.O>[CH3:11][O:10][C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[B:21]([OH:22])[OH:20]Participants
8
Conditions
- Temperature
- -78 °C
Procedure
576 μl of 1-bromo-2,4-dimethoxybenzene was dissolved in 5.8 ml of tetrahydrofuran and 3 ml of 1.6 mol/l solution of n-butyl lithium in hexane was added dropwise at −78° C. under argon atmosphere. Then, 1.1 ml of triisopropylborate was added, and after stirred at −78° C. for 40 minutes, the mixture was stirred at room temperature for 2 hours. To the reaction mixture, 40 ml of water and 1 ml of 5N-hydrochloric acid was added, and extracted with 50 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to yield 610.2 mg of the title compound.
Workup
- stirringthe mixture was stirred at room temperature for 2 hours
- extractionextracted with 50 ml of ethyl acetate
- dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
- custompurified by silica gel column chromatography (hexane:ethyl acetate=2:1)
Sources & evidence
- ORD record
- ord-2b9fb88b0665469586ade850be34e3ca
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889727B2
Reaction notes
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