Oxalyl chloride → 2-[1-(2-Bromo-5-methoxy-phenyl)-cyclopropyl]-benzofuran

HRID 61924ノート

反応式

HRID 61924 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1([C:13]([OH:15])=O)[CH2:12][CH2:11]1.C(Cl)(=O)C(Cl)=O.[Br-].O[C:24]1[CH:49]=[CH:48][CH:47]=[CH:46][C:25]=1[CH2:26][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>CN(C=O)C.C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1([C:13]2[O:15][C:24]3[CH:49]=[CH:48][CH:47]=[CH:46][C:25]=3[CH:26]=2)[CH2:11][CH2:12]1

参加物

6

反応物 3

HCID 65578Oxalyl chlorideHCID 2724142(2-Hydroxybenzyl)triphenylphosphonium bromideHCID 668347871-(2-Bromo-5-methoxyphenyl)cyclopropane-1-carboxylic acid

生成物 1

HCID 668344012-[1-(2-Bromo-5-methoxy-phenyl)-cyclopropyl]-benzofuran収率 81.8%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒

実験手順

To the DCM solution (6 ml) of 1-(2-bromo-5-methoxy-phenyl)-cyclopropane carboxylic acid (0.3 g, 1.1 mmol), DMF (2 drops) and oxalyl chloride (0.23 ml, 2.5 mmol) were added at room temperature, and the mixture was stirred at room temperature for 2 hrs. The residues obtained from the reaction solution after concentration under reduced pressure were dissolved in toluene (6 ml), added with (2-hydroxybenzyl)triphenylphosphonium bromide (0.605 g, 1.32 mmol) and TEA (0.46 ml, 3.3 mmol), and the resulting mixture was stirred and heated at 100° C. overnight. The residues obtained after concentration under reduced pressure were purified by silica gel column (hexane:DCM) to obtain the title compound (0.309 g, 81%).

後処理

  1. customThe residues obtained from the reaction solution
  2. concentrationafter concentration under reduced pressure
  3. dissolutionwere dissolved in toluene (6 ml)
  4. stirringthe resulting mixture was stirred
  5. temperatureheated at 100° C. overnight
  6. customThe residues obtained
  7. concentrationafter concentration under reduced pressure
  8. customwere purified by silica gel column (hexane:DCM)

出典と根拠

ORDレコード
ord-a3af345e73a24b86a904738f4e68d255
出典データセット
uspto-grants-2016_09
特許番号
US09440922B2

反応ノート

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