1-Bromo-1-chloroethane → 1-(3,4-Dichlorophenyl)cyclopropanecarbonitrile

HRID 32494

反応式

HRID 32494 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]#[N:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH:13](Cl)[CH3:14].[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:10]#[N:11])[CH2:14][CH2:13]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

6

反応物 3

HCID 116541-Bromo-1-chloroethaneHCID 14798Sodium HydroxideHCID 76690(3,4-Dichlorophenyl)acetonitrile

生成物 1

HCID 116009391-(3,4-Dichlorophenyl)cyclopropanecarbonitrile収率 102.4%

試薬・触媒・溶媒 2

HCID 66133Benzyl triethylammonium chloride触媒HCID 962Water溶媒

実験手順

To a stirred mixture of 3,4-Dichloro-phenylacetonitrile (4.65 g. 25 mmol) triethylbenzylammonium chloride (0.2 g) and 1-bromochoroethane (4.2 ml, 50 mmol), 50% sodium hydroxide (16 ml, 200 mmol) was added dropwise at 50° then the reaction was stirred at 50° for 10 hrs. After cooling to rt, the reaction mixture was diluted with water and extracted with EtOAc (×3). The layers were separated, washed with water (×3) and brine, then dried over MgSO4. Evaporation of the solvent under reduced pressure afforded the title compound (5.43 g) which was then recrystallized from Et2O/hexanes as a pale pink solid (4.49 g, 85%). Lc/MS(ES) m/e 212 [M+H]+.

後処理

  1. additionwas added dropwise at 50°
  2. extractionextracted with EtOAc (×3)
  3. customThe layers were separated
  4. washwashed with water (×3) and brine
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent under reduced pressure

出典と根拠

ORDレコード
ord-96c9846e5de44999b12d97648020fbad
出典データセット
uspto-grants-2008_09
特許番号
US07427623B2

関連ノート

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