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

HRID 217264ノート

反応式

HRID 217264 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-570703af8cd14b91be69f2555fbda542
出典データセット
uspto-grants-2012_06
特許番号
US08193372B2

反応ノート

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