Diethyl Ether → (Chloromethyl)(4-fluorophenyl)dimethylsilane

HRID 428808Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1.[Cl:14][CH2:15][Si:16]([CH3:19])([CH3:18])Cl.C(OCC)C>O1CCCC1>[Cl:14][CH2:15][Si:16]([CH3:19])([CH3:18])[C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1

Participants

Conditions

Temperature: -70 °C

Procedure

250 ml of n-butyl lithium (1.6M in hexane) are added to 39 ml of 4-bromo-fluoro-benzene in 400 ml of tetrahydrofuran within a period of 45 minutes with stirring at −70° C. The mixture is stirred for a further 30 minutes and then 53 ml of chloromethyl-dimethyl-chlorosilane dissolved in 50 ml of tetrahydrofuran are added dropwise. The mixture is stirred at −70° C. for a further 30 minutes and the temperature of the reaction mixture is then allowed to rise to 0° C. The reaction mixture is poured onto 200 ml of ice, and 300 ml of diethyl ether are added; the mixture is washed with water and saturated sodium chloride solution and dried over sodium sulfate; the solvent is evaporated off in vacuo. Distillation of the residue at 97-105° C. (21 mbar) yields the title product.

Workup

stirringThe mixture is stirred for a further 30 minutes
additionare added dropwise
stirringThe mixture is stirred at −70° C. for a further 30 minutes
customto rise to 0° C
additionare added
washthe mixture is washed with water and saturated sodium chloride solution
dry with materialdried over sodium sulfate
customthe solvent is evaporated off in vacuo
distillationDistillation of the residue at 97-105° C. (21 mbar)

Sources & evidence

ORD record: ord-7761177b02344e708f1b6abc96c8ffe0
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313344B1

Reaction notes

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