N-bromobutanimide → 2-[(5-Bromo-2-chloro-3-fluorophenyl)oxy]-4-(bromomethyl)-1-chloro-3-fluorobenzene

HRID 1874912ノート

反応式

HRID 1874912 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([F:19])[C:5]([Cl:18])=[C:6]([O:8][C:9]2[C:14]([F:15])=[C:13]([CH3:16])[CH:12]=[CH:11][C:10]=2[Cl:17])[CH:7]=1.C1C(=O)N([Br:27])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:1][C:2]1[CH:3]=[C:4]([F:19])[C:5]([Cl:18])=[C:6]([O:8][C:9]2[C:14]([F:15])=[C:13]([CH2:16][Br:27])[CH:12]=[CH:11][C:10]=2[Cl:17])[CH:7]=1

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 684864972-[(5-Bromo-2-chloro-3-fluorophenyl)oxy]-1-chloro-3-fluoro-4-methylbenzene

生成物 1

HCID 866448922-[(5-Bromo-2-chloro-3-fluorophenyl)oxy]-4-(bromomethyl)-1-chloro-3-fluorobenzene収率 62.4%

試薬・触媒・溶媒 2

HCID 6547Azobisisobutyronitrile触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

2-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-1-chloro-3-fluoro-4-methylbenzene (13.25 g, 36.0 mmol) and NBS (6.41 g, 36.0 mmol) were combined in carbon tetrachloride (150 mL) with a catalytic amount of AIBN (0.296 g, 1.800 mmol) and stirred at reflux for 16 h. The reaction mixture was washed with water, dried over MgSO4, filtered and concentrated to dryness. The residue was purified by chromatography on 330 g silica gel eluted with 0 to 10% Et2O in hexanes to give the desired product, 2-[(5-bromo-2-chloro-3-fluorophenyl)oxy]-4-(bromomethyl)-1-chloro-3-fluorobenzene (10.04 g, 22.47 mmol, 62.4% yield), as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.53-7.67 (m, 3H), 6.78 (s, 1H), 4.75 (s, 2H).

後処理

  1. temperatureat reflux for 16 h
  2. washThe reaction mixture was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by chromatography on 330 g silica gel
  7. washeluted with 0 to 10% Et2O in hexanes

出典と根拠

ORDレコード
ord-ca351a5edb2b4d23aa0aa46920519ffa
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

読み込み中…