Dimethyl Sulfoxide → α,α-Difluorobenzeneacetaldehyde

HRID 1810057Notes

Reaction equation

HRID 1810057 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]([F:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:13][OH:14].C(N(CC)CC)C>C(Cl)Cl.O>[F:11][C:12]([F:21])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[CH:13]=[O:14]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 97938912,2-Difluoro-2-phenylethanol

Product 1

HCID 14644933α,α-DifluorobenzeneacetaldehydeYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of oxalyl chloride (2.66 g, 21.0 mmol) in DCM (300 mL) was added DMSO (2.5 mL, 35.0 mmol) at 60° C. The mixture was stirred for 30 min. Then 2,2-difluoro-2-phenyl-ethanol (28.1 g, 18.0 mmol) was added at the same temperature. The mixture was stirred for another 30 min. Triethylamine (11.1 mL, 80.0 mmol) was added and then the mixture was stirred for 2 h at room temperature. Water was added and the organic layer was dried over anhydrous sodium sulfate and concentrated to obtain the crude product difluoro-phenyl-acetaldehyde (828 mg, 30%), which was used to the next step without further purification.

Workup

  1. stirringThe mixture was stirred for another 30 min
  2. stirringthe mixture was stirred for 2 h at room temperature
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-010b8b1da4e74894a23baefb98219526
Source dataset
uspto-grants-2013_01
Patent number
US08362049B2

Reaction notes

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