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

HRID 2170716노트

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HRID 2170716 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

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온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6684f7a224ba4610bd72a6910d63fa99
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051265B2

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