Dimethyl Sulfoxide → trans-2-(4-Bromophenyl)cyclopropane-1-carbaldehyde

HRID 73297

Reaction equation

HRID 73297 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C@H:18]2[CH2:20][C@@H:19]2[CH2:21][OH:22])=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([C@H:18]2[CH2:20][C@@H:19]2[CH:21]=[O:22])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 57515373((1S,2S)-2-(4-bromophenyl)cyclopropyl)methanol

Product 1

HCID 57515374trans-2-(4-Bromophenyl)cyclopropane-1-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

DMSO (3 equivalents) was added dropwise to a solution of oxalyl chloride in anhydrous dichloromethane under N2 at −78° C. A solution of the alcohol from Example 28B ((1S,2S)-[2-(4-bromophenyl)cyclopropyl]methanol) in dichloromethane was then added dropwise at −78° C. Stirring at this temperature was continued for 30 minutes, then triethylamine (4 equivalents) was added and the dry ice bath was removed. After stirring for 1 hour, the mixture was treated with saturated aqueous NH4Cl. The mixture was extracted with ether. The combined organic extracts was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by eluting through a pad of silica gel with hexane to provide the title compound.

Workup

  1. customthe dry ice bath was removed
  2. stirringAfter stirring for 1 hour
  3. additionthe mixture was treated with saturated aqueous NH4Cl
  4. extractionThe mixture was extracted with ether
  5. dry with materialThe combined organic extracts was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customThe residue was purified
  9. washby eluting through a pad of silica gel with hexane

Sources & evidence

ORD record
ord-085b4b5b2e29468f94533ee31bb0c49e
Source dataset
uspto-grants-2014_09
Patent number
US08829041B2

Linked notes

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