Azobisisobutyronitrile → 4-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}-3-fluorobenzonitrile

HRID 1875210

반응식

HRID 1875210 반응식
[Cl:1][C:2]1[C:7]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=2[F:17])=[C:6]([F:18])[C:5]([CH3:19])=[CH:4][CH:3]=1.C1C(=O)N([Br:27])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:27][CH2:19][C:5]1[C:6]([F:18])=[C:7]([O:8][C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][C:10]=2[F:17])[C:2]([Cl:1])=[CH:3][CH:4]=1

참가 물질

5

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 687209894-[(6-Chloro-2-fluoro-3-methylphenyl)oxy]-3-fluorobenzonitrile

생성물 1

HCID 687226214-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}-3-fluorobenzonitrile수율 52%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

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온도
80 °C

실험 절차

To a solution of 4-[(6-chloro-2-fluoro-3-methylphenyl)oxy]-3-fluorobenzonitrile (2.41 g, 8.62 mmol) and NBS (1.534 g, 8.62 mmol) in carbon tetrachloride (150 ml) was added AIBN (1.415 g, 8.62 mmol) and the reaction mixture was stirred at 80° C. overnight. The solvent was removed and the crude material was purified via silica gel chromatography to give 4-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}-3-fluorobenzonitrile (1.60 g, 4.46 mmol, 52% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.08 (dd, 1H), 7.62 (d, 1H), 7.48-7.59 (m, 2H), 6.92 (t, 1H), 4.70 (s, 2H).

후처리

  1. customThe solvent was removed
  2. customthe crude material was purified via silica gel chromatography

출처 및 근거

ORD 기록
ord-239265706bd24a09b1a3b27b29ac51d4
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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