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

HRID 1107716노트

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HRID 1107716 반응식
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]

참가 물질

6

반응물 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 5226685-Fluoro-2-methylbenzonitrileHCID 178418339Butyllithium

생성물 1

HCID 18785863Benzonitrile, 3-fluoro-6-methyl-2-(trimethylsilyl)-수율 94%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

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.

후처리

  1. temperaturethe mixture warmed to room temperature over 1 h
  2. customevaporated
  3. filtrationfiltered
  4. customEvaporation of the filtrate

출처 및 근거

ORD 기록
ord-25934cccc74b468aa9553b38ef4ba855
출처 데이터셋
uspto-grants-2000_05
특허 번호
US06063789

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