Azobisisobutyronitrile → 1-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}naphthalene

HRID 1875047노트

반응식

HRID 1875047 반응식
[Cl:1][C:2]1[C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)=[C:6]([F:19])[C:5]([CH3:20])=[CH:4][CH:3]=1.[Br:21]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:21][CH2:20][C:5]1[C:6]([F:19])=[C:7]([O:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[C:2]([Cl:1])=[CH:3][CH:4]=1

참가 물질

5

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 684882771-[(6-Chloro-2-fluoro-3-methylphenyl)oxy]naphthalene

생성물 1

HCID 684855581-{[3-(Bromomethyl)-6-chloro-2-fluorophenyl]oxy}naphthalene수율 45.5%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

To a solution of 1-[(6-chloro-2-fluoro-3-methylphenyl)oxy]naphthalene (1.69 g, 5.89 mmol) in carbon tetrachloride (20 mL) was added N-bromosuccinimide (1.154 g, 6.48 mmol) and AIBN (0.048 g, 0.295 mmol). The mixture was heated at reflux overnight. The reaction mixture was filtered through Celite and the solvent was evaporated. The residue was purified by flash chromatography (hexane:ethyl acetate) to give the desired product (0.98 g, 45.5%) as a light yellow oil. 1H NMR (400 MHz, chloroform-d) δ ppm 8.43-8.51 (m, 1H), 7.84-7.92 (m, 1H), 7.53-7.64 (m, 3H), 7.23-7.34 (m, 3H), 6.50 (d, 1H), 4.50 (d, 2H).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. filtrationThe reaction mixture was filtered through Celite
  4. customthe solvent was evaporated
  5. customThe residue was purified by flash chromatography (hexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-aedcfd401bbe4b488797dda86d99bc54
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304419B2

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