Triisopropyl borate → 3-Cyano-4-fluorophenylboronic acid
Reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[CH:9][C:10]([F:15])=[C:11]([CH:14]=1)[C:12]#[N:13].C([O:19][B:20](OC(C)C)[O:21]C(C)C)(C)C>O1CCCC1>[C:12]([C:11]1[CH:14]=[C:7]([B:20]([OH:21])[OH:19])[CH:8]=[CH:9][C:10]=1[F:15])#[N:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of n-butyllithium (5.6 ml, 2.5M in hexanes) was added over a 20 minute period to a solution of 5-bromo-2-fluorobenzonitrile and triisopropylborate (3.46 ml) in tetrahydrofuran (10 ml) at −78° C. The resulting solution was stirred at −78° C. for 30 minutes and then quenched by the addition of a 2M hydrochloric acid (20 ml) and extracted into ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by trituration using diethyl ether: hexane 1:2 to afford the sub-title compound as a solid (1.24 g).
Workup
- customquenched by the addition of a 2M hydrochloric acid (20 ml)
- extractionextracted into ethyl acetate
- dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by trituration
Sources & evidence
- ORD record
- ord-f93f9d2e3e17491dbfc44277a0ec05ad
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06300352B1
Reaction notes
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