N-bromobutanimide → 2-Bromomethyl-5-chloro-4-nitrobenzonitrile

HRID 1739835노트

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HRID 1739835 반응식
[Cl:1][C:2]1[C:3]([N+:11]([O-:13])=[O:12])=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[C:7]#[N:8].C1C(=O)N([Br:21])C(=O)C1>ClC1C=CC=CC=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:21][CH2:10][C:5]1[CH:4]=[C:3]([N+:11]([O-:13])=[O:12])[C:2]([Cl:1])=[CH:9][C:6]=1[C:7]#[N:8]

참가 물질

5

반응물 2

HCID 67184N-bromobutanimide2회HCID 102417995-Chloro-2-methyl-4-nitrobenzonitrile

생성물 1

HCID 154289152-Bromomethyl-5-chloro-4-nitrobenzonitrile수율 108.9%

시약·촉매·용매 2

HCID 7187Benzoyl Peroxide촉매2회HCID 7964Chlorobenzene용매

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온도
130 °C

실험 절차

A mixture of 5-chloro-4-nitro-2-methylbenzonitrile (32.0 g, 0.16 mol), NBS (54.0 g, 0.30 mol) and benzoyl peroxide (200 mg, catalytic amount) in chlorobenzene was heated at 130° C. and irradiated with a sunlamp for 15 h. More NBS (30.0 g, 0.17 mol) and benzoyl peroxide (200 mg) were added. The mixture was further reacted for 24 h. After cooling, the precipitate formed was filtered off and washed with CH2Cl2. The combined filtrates were washed with H2O (2×), dried over anhydrous MgSO4 and concentrated in vacuo. The residue was then chromatographed over silica gel and eluted with hexanes:EtOAc (9:1) to give 2-bromomethyl-5-chloro-4-nitrobenzonitrile (48 g, contaminated with starting material and dibrominated product) as a pale yellow solid.

후처리

  1. customirradiated with a sunlamp for 15 h
  2. customThe mixture was further reacted for 24 h
  3. temperatureAfter cooling
  4. customthe precipitate formed
  5. filtrationwas filtered off
  6. washwashed with CH2Cl2
  7. washThe combined filtrates were washed with H2O (2×)
  8. dry with materialdried over anhydrous MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was then chromatographed over silica gel
  11. washeluted with hexanes:EtOAc (9:1)

출처 및 근거

ORD 기록
ord-154b6c551aee4eeaa57aabc2ee6bcb65
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05968958

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