Triisopropyl borate → (5-Cyano-1-benzothiophen-2-yl)boronic acid
Reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([C:10]#[N:11])[CH:8]=[CH:9][C:2]1=2.C([Li])CCC.[B:17](OC(C)C)([O:22]C(C)C)[O:18]C(C)C>C1COCC1>[C:10]([C:7]1[CH:8]=[CH:9][C:2]2[S:1][C:5]([B:17]([OH:22])[OH:18])=[CH:4][C:3]=2[CH:6]=1)#[N:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a cold (−78° C.) solution of benzo[b]thiophene-5-carbonitrile (276 mg, 1.734 mmol) in anhydrous THF (5 mL) was added n-butyllithium (0.763 mL, 1.907 mmol) dropwise. The reaction mixture was stirred at −78° C. for 60 minutes. Next, a solution of triisopropyl borate (0.478 mL, 2.080 mmol) was added. The reaction mixture was stirred for 30 minutes stirring at −78° C. and then was allowed to warm to room temperature over a 2 hour period. Solvent was removed to give the title compound, which was used without purification or work up.
Workup
- stirringThe reaction mixture was stirred for 30 minutes
- stirringstirring at −78° C.
- temperatureto warm to room temperature over a 2 hour period
- customSolvent was removed
Sources & evidence
- ORD record
- ord-c964ed1377204c2e9b6f5bd9586267cd
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09056873B2
Reaction notes
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