Azobisisobutyronitrile → Methyl 3-(bromomethyl)thiophene-2-carboxylate

HRID 217264노트

반응식

HRID 217264 반응식
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8]

참가 물질

5

반응물 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 580757Methyl 3-methylthiophene-2-carboxylate

생성물 1

HCID 10537693Methyl 3-(bromomethyl)thiophene-2-carboxylate수율 68.6%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

A mixture of methyl 3-methylthiophene-2-carboxylate (13.2 mmol), N-Bromosuccinimide (13.2 mmol) and a catalytic amount of azobis-isobutyronitrile in carbon tetrachloride were heated at reflux under nitrogen. The reaction mixture was irradiated with a 500 W UV lamp for 1.5 hours, cooled down to room temperature and then filtered under autocup 0.45 μm, followed by the evaporation of the filtrate. The residue was purified by chromatography on silica gel (eluent: stepwise gradient of 3-5% diethyl ether in petroleum ether) to give 2.13 g of Intermediate IV.1 (69%), which was characterized by 1H NMR (CDCl3, 400 MHz) δ (ppm) 3.90 (s, 3H), 4.92 (s, 2H), 7.18 (d, J=5.3 Hz, 1H), 7.47 (d, J=5.3 Hz, 1H).

후처리

  1. temperatureat reflux under nitrogen
  2. customThe reaction mixture was irradiated with a 500 W UV lamp for 1.5 hours
  3. filtrationfiltered under autocup 0.45 μm
  4. customfollowed by the evaporation of the filtrate
  5. customThe residue was purified by chromatography on silica gel (eluent

출처 및 근거

ORD 기록
ord-570703af8cd14b91be69f2555fbda542
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193372B2

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