Azobisisobutyronitrile → 2-Chloro-5-(chloromethyl)-3-fluoropyridine

HRID 659972

반응식

HRID 659972 반응식
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[F:9].[Cl:10]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>ClC1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][Cl:10])=[CH:4][C:3]=1[F:9]

참가 물질

5

반응물 3

HCID 6547Azobisisobutyronitrile2회HCID 31398Chlorosuccinimide2회HCID 135413652-Chloro-3-fluoro-5-methylpyridine

생성물 1

HCID 216982012-Chloro-5-(chloromethyl)-3-fluoropyridine수율 53%

시약·촉매·용매 1

HCID 7964Chlorobenzene용매

실험 절차

1.00 g (6.87 mmol) of 6-chloro-5-fluoro-3-methylpyridine (cf. F. L. Setliff, Organic Preparations and Procedures International 1971, 3, 217-222), 1.01 g (7.56 mmol) of N-chlorosuccinimide and 0.11 g (0.69 mmol) of 2,2′-azobis(2-methylpropanenitrile) in 100 ml of chlorobenzene are boiled under reflux for 2 days. After about 16 and 32 hours, in each case a further 1.01 g (7.56 mmol) of N-chlorosuccinimide and 0.11 g (0.69 mmol) of 2,2′-azobis(2-methylpropanenitrile) are added. The reaction mixture is washed with saturated aqueous sodium sulphite solution and sodium bicarbonate solution and then dried over sodium sulphate and concentrated under reduced pressure. Column chromatography of the residue on silica gel (silica gel 60-Merck, particle size: 0.04 to 0.063 mm) using the mobile phase mixture ethyl acetate:cyclohexane (1:20) gives 0.65 g (53% of theory) 6-chloro-3-chloromethyl-5-fluoropyridine.

후처리

  1. temperatureunder reflux for 2 days
  2. washThe reaction mixture is washed with saturated aqueous sodium sulphite solution and sodium bicarbonate solution
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-7543eb0e29654cb8b29638f4505a423d
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084452B2

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