Azobisisobutyronitrile → 5-Bromomethyl-3-chloro-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene

HRID 2220283노트

반응식

HRID 2220283 반응식
[Cl:1][C:2]1[C:3]2[CH:26]=[C:25]([CH3:27])[CH:24]=[CH:23][C:4]=2[S:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:9]([C:19]([F:22])([F:21])[F:20])[CH:8]=1.C1C(=O)N([Br:35])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:35][CH2:27][C:25]1[CH:24]=[CH:23][C:4]2[S:5][C:6]([C:7]3[CH:12]=[CH:11][C:10]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=4)=[C:9]([C:19]([F:22])([F:21])[F:20])[CH:8]=3)=[C:2]([Cl:1])[C:3]=2[CH:26]=1

참가 물질

5

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 68453943HCID 68453943, 화합물

생성물 1

HCID 684526035-Bromomethyl-3-chloro-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene수율 38%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

To a solution of 3-chloro-5-methyl-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene(110 mg, 0.273 mmol) in CCl4 (3 ml) is added NBS (49 mg, 1 eq.). The mixture is heated at reflux for 15 minutes before AIBN (4.5 mg, 0.1 eq.) is added. The reaction is further heated at reflux overnight. The mixture is filtered through Celite and washed with CCl4. The filtrate is concentrated and purified by column chromatography (EtOAc/Hexane, gradient) to give 50 mg of 5-bromomethyl-3-chloro-2-(2-trifluoromethyl-biphenyl-4-yl)-benzo[b]thiophene in 38% yield.

후처리

  1. temperatureThe mixture is heated
  2. additionis added
  3. temperatureThe reaction is further heated
  4. temperatureat reflux overnight
  5. filtrationThe mixture is filtered through Celite
  6. washwashed with CCl4
  7. concentrationThe filtrate is concentrated
  8. custompurified by column chromatography (EtOAc/Hexane, gradient)

출처 및 근거

ORD 기록
ord-089b4286df884414b976180f25e29bc2
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417065B2

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