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

HRID 2275302Notes

Reaction equation

HRID 2275302 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-dea6a87af2e24481bcd47c382a250b06
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

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