1-Bromo-2-Chloroethane → 1-(3-Methylphenyl)cyclopropane-1-carbonitrile

HRID 2170716ノート

反応式

HRID 2170716 の反応式
[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]#[N:9])[CH:2]=1.[OH-].[Na+].Br[CH2:14][CH2:15]Cl>C1(C)C=CC=CC=1.O>[C:1]1([CH3:10])[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([C:8]#[N:9])[CH2:15][CH2:14]2)[CH:2]=1

参加物

6

反応物 3

HCID 78491-Bromo-2-ChloroethaneHCID 14798Sodium HydroxideHCID 76279m-Methylphenylacetonitrile

生成物 1

HCID 200261921-(3-Methylphenyl)cyclopropane-1-carbonitrile

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
60 °C

実験手順

To a stirred solution of 2-(m-tolyl)acetonitrile (4.2 g, 32 mmol) in toluene (15 mL) was added sodium hydroxide (30 mL, 50% w/w in water, 375 mmol), 1-bromo-2-chloroethane (9.3 mL, 112 mmol) and (n-Bu)4Br (0.5 g, 1.55 mmol). The mixture was heated at 60° C. overnight. After cooling to room temperature, the reaction mixture was diluted with water (40 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure and purified by silica gel chromatography to obtain the title compound.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc (3×50 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-6684f7a224ba4610bd72a6910d63fa99
出典データセット
uspto-grants-2015_06
特許番号
US09051265B2

反応ノート

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