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

HRID 1518248Notes

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 left stirring 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 left stirring 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 colorless oil (64% yield, 65% pure) which was used without further purification in the next reaction.

Workup

waitthe resulting mixture was left
temperatureto warm to RT overnight
waitthe resulting mixture was left
stirringstirring 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 colorless oil (64% yield, 65% pure) which
customwas used without further purification in the next reaction

Sources & evidence

ORD record: ord-6bd34ecbd1284eb5b8f2f0048d99f7dc
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232390B2

Reaction notes

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