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

HRID 61924Notes

Reaction equation

HRID 61924 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 66834787HCID 66834787, compound

Product 1

HCID 668344012-[1-(2-Bromo-5-methoxyphenyl)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-a3af345e73a24b86a904738f4e68d255
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

Loading…