Dichloromethane → (1-(4-Bromo-2-fluorophenyl)cyclopropoxy)(tert-butyl)dimethylsilane

HRID 1842901Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:11])[CH2:10][CH2:9]2)=[C:4]([F:12])[CH:3]=1.C(Cl)Cl.[CH3:16][C:17]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])[CH3:18]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([O:11][Si:20]([C:17]([CH3:19])([CH3:18])[CH3:16])([CH3:22])[CH3:21])[CH2:9][CH2:10]2)=[C:4]([F:12])[CH:3]=1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 28928tert-Butyldimethylsilyl chloride

HCID 626689571-(4-Bromo-2-fluorophenyl)cyclopropan-1-ol

Product 1

HCID 70816354(1-(4-Bromo-2-fluorophenyl)cyclopropoxy)(tert-butyl)dimethylsilane

Procedure

To a stirred solution of 1-(4-bromo-2-fluorophenyl)cyclopropanol (9.01 g, 39.0 mmol, 1 eq) in DCM (100 mL) imidazole (5.33 g, 78 mmol, 2 eq) was added at 0° C. followed by TBDMSCl (7.08 g, 46.8 mmol, 1.2 eq) and the reaction mixture was stirred for 3 h. The reaction mixture was washed with water (100 mL), brine (100 mL), dried over Na2SO4 and the solvent was evaporated to get (1-(4-bromo-2-fluorophenyl)cyclopropoxy)(tert-butyl)dimethylsilane which was purified by CC using PE as eluent to yield pure (1-(4-bromo-2-fluorophenyl)cyclopropoxy)(tert-butyl)dimethylsilane (9.01 g, 67%; TLC system: PE, Rf: 0.8) as a colourless oil.

Workup

washThe reaction mixture was washed with water (100 mL), brine (100 mL)
dry with materialdried over Na2SO4
customthe solvent was evaporated

Sources & evidence

ORD record: ord-0718ea10865c4a8e894d3dcadc31757a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946204B2

Reaction notes

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