Hydrochloric Acid → (4-{[Tert-butyl(dimethyl)silyl]oxy}-2-methoxyphenyl)boronic acid

HRID 2426745Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:20]=[CH:19][C:10]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])=[CH:9][C:8]=1[O:21][CH3:22].[B:23](OC(C)C)([O:28]C(C)C)[O:24]C(C)C.Cl>C1COCC1.CCCCCC>[Si:12]([O:11][C:10]1[CH:19]=[CH:20][C:7]([B:23]([OH:28])[OH:24])=[C:8]([O:21][CH3:22])[CH:9]=1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

Conditions

Temperature: -75 °C

Procedure

In an atmosphere of nitrogen, n-butyl lithium (a hexane solution) was added at −75° C. to a THF solution of (4-bromo-3-methoxyphenoxy)(tert-butyl)dimethylsilane, followed by stirring at −75° C. for 1 hour. Triisopropyl borate was added to the reaction mixture, followed by stirring at room temperature for 30 minutes. The reaction mixture was treated with hydrochloric acid to obtain (4-{[tert-butyl(dimethyl)silyl]oxy}-2-methoxyphenyl)boronic acid.

Workup

stirringby stirring at room temperature for 30 minutes

Sources & evidence

ORD record: ord-6c0a4b86fe0c4999b49d9eacf6bf06da
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07968552B2

Reaction notes

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