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

HRID 2275302
ノート
印刷プレビュー

反応式

HRID 2275302 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
参加物実験手順後処理出典と根拠反応ノート

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 6344
Dichloromethane
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-dea6a87af2e24481bcd47c382a250b06
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09126931B2

反応ノート

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