Oxalyl chloride → Methyl 2-bromothiophene-3-carboxylate

HRID 604362ノート

反応式

HRID 604362 の反応式
[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([OH:9])=[O:8].[C:10](Cl)(=O)C(Cl)=O>C(Cl)Cl.CN(C=O)C>[Br:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

参加物

5

反応物 2

HCID 65578Oxalyl chlorideHCID 123209712-Bromo-3-thiophenecarboxylic acid

生成物 1

HCID 53302196Methyl 2-bromothiophene-3-carboxylate収率 98.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

2-bromo-3-thiophene carboxylic acid (1.0 eq, 12.56 g, 60.66 mmol) was suspended in CH2Cl2 (200 ml). Oxalyl chloride (1.1 eq, 5.9 ml, 67.16 mmol) and 5 drops of DMF were added, inducing formation of gas. The mixture was stirred overnight at room temperature and the volatiles were removed in vacuo. The resulting solid was suspended in dry methanol (150 ml) and the mixture heated to ebullition. Evaporation of the solvents afforded methyl 2-bromo-3-thiophene carboxylate (13.16 g, 98% yield) as a crude brown oil. LCMS (ES): 99% pure, m/z not detected; 1H NMR (CDCl3, 400 MHz) δ 3.88 (s, 3H), 7.23 (d, J=5.6, 1H), 7.56 (d, J=5.6, 1H) ppm.

後処理

  1. customthe volatiles were removed in vacuo
  2. temperaturethe mixture heated to ebullition
  3. customEvaporation of the solvents

出典と根拠

ORDレコード
ord-4b1289f312a6478c94e85d2d5f89a29f
出典データセット
uspto-grants-2011_03
特許番号
US07910600B2

反応ノート

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