Tetrahydrofuran → [3,4-Dimethoxy-2-(methoxymethyl)phenyl]boronic acid
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](OC)=[C:4]([O:10][CH3:11])[C:3]=1[O:12][CH2:13]OC.C([Li])CCC.CO[B:23]([O:26]C)[O:24]C.[O:28]1[CH2:32]CC[CH2:29]1>>[CH3:11][O:10][C:4]1[C:5]([CH2:29][O:28][CH3:32])=[C:6]([B:23]([OH:24])[OH:26])[CH:7]=[CH:2][C:3]=1[O:12][CH3:13]Participants
5
Conditions
- Temperature
- -78 °C
Procedure
To a stirring solution of 1-bromo-3,4-dimethoxy-2-methoxymethoxy-benzene (1 g, 3.62 mmol) in tetrahydrofuran (15 mL) at −78° C., was added n-butyllithium (5.5 mL, 7.24 mmol) and stirred for 20 min to this trimethylborate (3.76 g, 36.23 mmol) was added and the resultant reaction mixture was stirred for 30 min at −78° C. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 3,4-dimethoxy-2-(methoxymethyl)phenylboronic acid as a solid.
Workup
- additionwas added
- customthe resultant reaction mixture
- customThe reaction mixture was quenched with saturated ammonium chloride solution
- extractionextracted with ethyl acetate (3×)
- washThe combined ethyl acetate layer was washed with brine
- dry with materialdried over anhydrous sodium sulphate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d9cd85bb11fb41b6881b1ca274ea02e3
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09051290B2
Reaction notes
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