Hydrochloric Acid → B-(3-Cyano-4-methoxyphenyl)boronic acid
Reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[CH:9][C:10]([O:15][CH3:16])=[C:11]([CH:14]=1)[C:12]#[N:13].C([O:20][B:21](OC(C)C)[O:22]C(C)C)(C)C.Cl>O1CCCC1>[C:12]([C:11]1[CH:14]=[C:7]([B:21]([OH:22])[OH:20])[CH:8]=[CH:9][C:10]=1[O:15][CH3:16])#[N:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -20 °C
Procedure
16.23 ml of n-butyllithium solution (1.6M in hexane) are added dropwise to a solution of 5.00 g of 5-bromo-2-methoxybenzonitrile in 90 ml of dry tetrahydrofuran at −78° C. After stirring at this temperature for 45 minutes, 6.71 ml of triisopropylborate are added, and the mixture is then slowly warmed to −20° C. 50 ml of 1N HCl are added to the reaction mixture. The phase is separated and the aqueous phase is extracted three more times with 100 ml of diethyl ether each time. The combihled organic phases are dried with sodium sulphate, filtered and evaporated. The remaining oil is mixed with pentane, and the precipitate which separates out is filtered off with suction and washed once with a little dichloromethane. Drying under high vacuum affords the title compound as a white solid. Rt=2.74.
Workup
- customThe phase is separated
- extractionthe aqueous phase is extracted three more times with 100 ml of diethyl ether each time
- dry with materialThe combihled organic phases are dried with sodium sulphate
- filtrationfiltered
- customevaporated
- additionThe remaining oil is mixed with pentane
- filtrationthe precipitate which separates out is filtered off with suction
- washwashed once with a little dichloromethane
- customDrying under high vacuum
Sources & evidence
- ORD record
- ord-869e57b01e2141c6a6e6e3d243220d9d
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07799779B2
Reaction notes
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