Azobisisobutyronitrile → Ethyl 2-[4-(bromomethyl)phenyl]-4,4,4-trifluoro-3-methylbutanoate

HRID 1475640노트

반응식

HRID 1475640 반응식
[F:1][C:2]([F:19])([F:18])[CH:3]([CH3:17])[CH:4]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:20]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClC(Cl)Cl>[Br:20][CH2:16][C:13]1[CH:12]=[CH:11][C:10]([CH:4]([CH:3]([CH3:17])[C:2]([F:18])([F:19])[F:1])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:15][CH:14]=1

참가 물질

5

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 58136599Ethyl 4,4,4-trifluoro-3-methyl-2-(4-methylphenyl)butanoate

생성물 1

HCID 58136537Ethyl 2-[4-(bromomethyl)phenyl]-4,4,4-trifluoro-3-methylbutanoate

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

2.25 g (8.2 mmol) of ethyl 4,4,4-trifluoro-3-methyl-2-(4-methylphenyl)butanoate, 1.53 g (8.6 mmol) of N-bromosuccinimide and 67 mg (0.41 mmol) of 2,2′-azobis-(2-methylpropanenitrile) in 36 ml of trichloromethane were stirred under reflux overnight. After the reaction had gone to completion, the succinimide was filtered off, the filter residue was washed with dichloromethane and the filtrate was concentrated under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 40:1). This gave 2.667 g (7.5 mmol, 92% of theory) of a yellowish oil.

후처리

  1. temperatureunder reflux overnight
  2. filtrationthe succinimide was filtered off
  3. washthe filter residue was washed with dichloromethane
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 40:1)

출처 및 근거

ORD 기록
ord-0a3438fff52f4744b68641c2c3753a00
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018258B2

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