N-bromobutanimide → 3-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}-2,5-dichlorobenzonitrile

HRID 1874894ノート

反応式

HRID 1874894 の反応式
[Cl:1][C:2]1[C:9]([O:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]([CH3:18])[C:12]=2[F:19])=[CH:8][C:7]([Cl:20])=[CH:6][C:3]=1[C:4]#[N:5].C1C(=O)N([Br:28])C(=O)C1>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:28][CH2:18][C:13]1[C:12]([F:19])=[C:11]([O:10][C:9]2[C:2]([Cl:1])=[C:3]([CH:6]=[C:7]([Cl:20])[CH:8]=2)[C:4]#[N:5])[C:16]([Cl:17])=[CH:15][CH:14]=1

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 684840922,5-Dichloro-3-[(6-chloro-2-fluoro-3-methylphenyl)oxy]benzonitrile

生成物 1

HCID 684833023-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}-2,5-dichlorobenzonitrile収率 51.7%

試薬・触媒・溶媒 2

HCID 6547Azobisisobutyronitrile触媒HCID 5943Carbon Tetrachloride溶媒

実験手順

2,5-dichloro-3-[(6-chloro-2-fluoro-3-methylphenyl)oxy]benzonitrile (1.01 g, 3.06 mmol) and NBS (0.544 g, 3.06 mmol) were combined in carbon tetrachloride (30 mL) with a catalytic amount of AIBN (0.025 g, 0.153 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 80 g silica gel eluted with 0 to 10% Et2O in hexanes to give the 3-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}-2,5-dichlorobenzonitrile (0.647 g, 1.580 mmol, 51.7% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.03 (d, J=2.20 Hz, 1H), 7.53-7.64 (m, 2H), 7.29 (d, J=1.92 Hz, 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 80 g silica gel
  7. washeluted with 0 to 10% Et2O in hexanes

出典と根拠

ORDレコード
ord-c27139b022f34236a04ed3260cae1311
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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