N-bromobutanimide → 2-Azido-1-(bromomethyl)-4-iodobenzene

HRID 1869753노트

반응식

HRID 1869753 반응식
[N:1]([C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[CH3:11])=[N+:2]=[N-:3].[Br:12]N1C(=O)CCC1=O>C1C=CC=CC=1>[N:1]([C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[CH:6][C:5]=1[CH2:11][Br:12])=[N+:2]=[N-:3]

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 579875492-Azido-4-iodo-1-methylbenzene

생성물 1

HCID 579873052-Azido-1-(bromomethyl)-4-iodobenzene수율 67.4%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

A mixture of the azide from step 1 (9.1 g, 0.035M), N-Bromosuccinimide (6.8 g, 0.039M) and 1,1azobis(cyclohexanecarbonitrile) (0.85 g, 3.5 mmol) in benzene (40 ml) was heated at reflux overnight. The solvent was evaporated under vacuum and the residue was diluted EtOAc (100 ml) and washed with water (50 ml) and brine, dried (MgSO4) and concentrated under vacuum. The residue was purified by chromatography (silica, hexanes) to give the azide as a white solid (8 g, 67%). 1H NMR (500 MHz, CDCl3): δ 4.30 (2H, s), 6.98 (1H, d, J 8.0), 7.35 (2H, t, J 7.0).

후처리

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customThe solvent was evaporated under vacuum
  4. washwashed with water (50 ml) and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by chromatography (silica, hexanes)

출처 및 근거

ORD 기록
ord-2712c556c46f4892a5de18991fb307c6
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638629B2

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