tert-Butyldimethylsilyl chloride → HCID 11209312, compound

HRID 2378240Notes

Reaction equation

HRID 2378240 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.C(N(C(C)C)C(C)C)C.[C:20]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])([CH3:22])[CH3:21]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][Si:24]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:26])[CH3:25])=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 2622344-Bromo-2-methoxyphenol

Product 1

HCID 11209312HCID 11209312, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-2-methoxyphenol (2.87 g, 14.13 mmol) in DMF (20 ml) was added ethyldiisopropylamine (6.15 ml, 35.32 mmol). The clear solution was stirred for 5 min. followed by addition of tert-butylchlorodimethylsilane (2.56 g, 16.95 mmol). The crude was purified via flash column chromatography (100% in hexane) to give (4-bromo-2-methoxy-phenoxy)-tert-butyl-dimethyl-silane as a clear oil (4.45 g, 99%): 1HNMR (CDCl3) δ 6.95 (s, wide, 1H, Ar), 6.92 (d, J=2 Hz, 1H, Ar), 6.71 (d, J=7 Hz, 1H, Ar), 3.79 (s, 3H, OCH3), 0.98 (s, 9H, 3CH3), 0.13 (s, 6H, 2CH3). The product was carried over to the next step.

Workup

  1. customThe crude was purified via flash column chromatography (100% in hexane)

Sources & evidence

ORD record
ord-c73f5d89f33147a88408d713ede87ca4
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

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