Chlorotrimethylsilane → Benzonitrile, 3-fluoro-6-methyl-2-(trimethylsilyl)-

HRID 1107716Notes

Reaction equation

C([Li])CCC.C(NC(C)C)(C)C.[F:13][C:14]1[CH:15]=[C:16]([C:19]([CH3:22])=[CH:20][CH:21]=1)[C:17]#[N:18].[CH3:23][Si:24](Cl)([CH3:26])[CH3:25]>C1COCC1>[F:13][C:14]1[C:15]([Si:24]([CH3:26])([CH3:25])[CH3:23])=[C:16]([C:19]([CH3:22])=[CH:20][CH:21]=1)[C:17]#[N:18]

Participants

Conditions

Temperature: -78 °C

Procedure

n-Butyllithium (1.40M in hexanes, 11.8 mmol, 8.44 ml) was added dropwise to a stirred solution of diisopropylamine (1.84 ml) in THF (5 ml) at 0° C. After 30 min., the solution was cooled to -78° C. and 3-fluoro-6-methylbenzonitrile (1.60 g, 11.8 mmol) in THF (5 ml) was added dropwise. The pale purple anion was stirred for 20 min., trimethylsilylchoride (3.0 ml, 24 mmol) was added and the mixture warmed to room temperature over 1 h, evaporated, the residue taken up in a small amount of diethyl ether and filtered. Evaporation of the filtrate gave an off-white crystalline solid (2.3 g), m.p. 71-73° C.

Workup

temperaturethe mixture warmed to room temperature over 1 h
customevaporated
filtrationfiltered
customEvaporation of the filtrate

Sources & evidence

ORD record: ord-25934cccc74b468aa9553b38ef4ba855
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06063789

Reaction notes

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