Hexane → 4-Borono-3-methylbenzoic acid
Reaction equation
Br[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11].C([Li])CCC.CCCCCC.C([O:26][B:27](OC(C)C)[O:28]C(C)C)(C)C>C1COCC1.O>[B:27]([C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[CH3:11])([OH:28])[OH:26]Participants
7
Conditions
- Temperature
- -78 °C
Procedure
A stirred solution of 4-bromo-3-methylbenzoic acid (5.0 g, 0.020 mole) in dry THF (250 ml) at -78° C. under argon was treated with 1.6M n-butyllithium in hexane (36 ml, 0.057 mole). After 15 minutes, the reaction mixture was treated with triisopropylborate (13.4 ml, 0.050 mole), then stirred at -78° C. for 1 h, followed by room temp. for 19 h. The mixture was treated with water (25 ml), then concentrated in vacuo and the residue chromatographed on silica gel eluting with 10% methanol/dichloromethane to afford the title compound as a white solid (2.63 g, 67%).
Workup
- waitfollowed by room temp. for 19 h
- concentrationconcentrated in vacuo
- customthe residue chromatographed on silica gel eluting with 10% methanol/dichloromethane
Sources & evidence
- ORD record
- ord-42bdc218f7904793a8717d11af8db65b
- Source dataset
- uspto-grants-1998_09
- Patent number
- US05801170
Reaction notes
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