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

HRID 1869753ノート

反応式

HRID 1869753 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 579873052-Azido-1-(bromomethyl)-4-iodobenzene収率 67.4%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2712c556c46f4892a5de18991fb307c6
出典データセット
uspto-grants-2009_12
特許番号
US07638629B2

反応ノート

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