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

HRID 1107716ノート

反応式

HRID 1107716 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-25934cccc74b468aa9553b38ef4ba855
出典データセット
uspto-grants-2000_05
特許番号
US06063789

反応ノート

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