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

HRID 2275302
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HRID 2275302 반응식
[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
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참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매
HCID 6344
Dichloromethane
용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-dea6a87af2e24481bcd47c382a250b06
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09126931B2

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