Hydrochloric Acid → (4-Methoxy-2-{[(triisopropylsilyl)oxy]methyl}phenyl)boronic acid

HRID 1669429Notes

Reaction equation

Br[C:2]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:3]=1[CH2:4][O:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8].[Li]CCCC.[B:27](OC(C)C)([O:32]C(C)C)[O:28]C(C)C.Cl>C1COCC1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:2]([B:27]([OH:32])[OH:28])=[C:3]([CH2:4][O:5][Si:6]([CH:13]([CH3:15])[CH3:14])([CH:10]([CH3:12])[CH3:11])[CH:7]([CH3:9])[CH3:8])[CH:16]=1

Participants

Conditions

Temperature: -78 °C

Procedure

[(2-bromo-5-methoxybenzyl)oxy](triisopropyl)silane (1 eq) was dissolved in anhydrous THF (0.43M solution) and the solution was cooled to −78° C. A solution of n-BuLi (1.6M in hexanes, 1.05 eq) was added and the resulting mixture was stirred for 1 h at −78° C. Then triisopropyl borate (50% in THF, 1.3 eq) was added dropwise and the mixture was allowed to warm to RT overnight. 1N HCl was added and the resulting mixture was stirred at RT for 30 min. THF was removed in vacuo and replaced with Et2O. The organic phase was washed with water and with brine, then dried over Na2SO4 and evaporated in vacuo. The product was obtained as a colourless oil (64% yield, 65% pure) which was used without further purification in the next reaction.

Workup

temperatureto warm to RT overnight
stirringthe resulting mixture was stirred at RT for 30 min
customTHF was removed in vacuo
washThe organic phase was washed with water and with brine
dry with materialdried over Na2SO4
customevaporated in vacuo
customThe product was obtained as a colourless oil (64% yield, 65% pure) which
customwas used without further purification in the next reaction

Sources & evidence

ORD record: ord-1eec718ce26542e4a809d7f8da6a42ad
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989438B2

Reaction notes

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