Hydrochloric Acid → 3,5-Dimethylbiphenyl-4-ylboronic acid
Reaction equation
C([Li])(C)(C)C.[CH3:6][C:7]1[CH:8]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:10]=[C:11]([CH3:13])[CH:12]=1.C[O:21][B:22](OC)[O:23]C.Cl>O1CCCC1>[CH3:6][C:7]1[C:12]([B:22]([OH:23])[OH:21])=[C:11]([CH3:13])[CH:10]=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
t-Butyllithium (1.7 M solution in hexane, 36.2 ml, 61.6 mmol) is added dropwise to a solution of 3,5-dimethylbiphenyl (7.27 g, 28 mmol) in dry tetrahydrofuran (150 ml) at −78° C. under an atmosphere of nitrogen. The reaction mixture is stirred at −78° C. for 30 minutes, then trimethylborate (9.54 ml, 84 mmol) is added. The resulting mixture is stirred at −78° C. for 30 minutes and then allowed to warm to room temperature. The reaction mixture is acidified with 10% aqueous hydrochloric acid solution and extracted with diethyl ether. The organic layers are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated to dryness to give a yellow solid. The crude product is triturated with isohexane and filtered to give 3,5-dimethylbiphen-4-ylboronic acid.
Workup
- stirringThe resulting mixture is stirred at −78° C. for 30 minutes
- temperatureto warm to room temperature
- extractionextracted with diethyl ether
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe filtrate is evaporated to dryness
- customto give a yellow solid
- customThe crude product is triturated with isohexane
- filtrationfiltered
Sources & evidence
- ORD record
- ord-6caec6d3f6cf4c6ca569741db185156f
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08940913B2
Reaction notes
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