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

HRID 1874894노트

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HRID 1874894 반응식
[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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 6547Azobisisobutyronitrile촉매HCID 5943Carbon Tetrachloride용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c27139b022f34236a04ed3260cae1311
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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