Dimethyl Sulfoxide → 2-(4-Fluorophenyl)-2-methylpropanal

HRID 1944055Notes

Reaction equation

HRID 1944055 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:22])([CH3:21])[CH2:19][OH:20])=[CH:14][CH:13]=1.CCN(CC)CC>C(Cl)Cl>[F:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]([CH3:22])([CH3:21])[CH:19]=[O:20])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 212628022-(4-Fluorophenyl)-2-methylpropan-1-ol

Product 1

HCID 820747502-(4-Fluorophenyl)-2-methylpropanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of DMSO (1.7 eq.) in DCM (0.5 M) was treated at −78° C. with a 2 M solution of oxalyl chloride in DCM (1.4 eq.). The reaction was stirred for 5 min, and a solution of 2-(4-fluorophenyl)-2-methylpropan-1-ol (1 eq.) in DCM (3 M) added to the reaction mixture. After stirring for 10 min, NEt3 (2.4 eq.) was added and the reaction mixture warmed to 0° C., stirred one hour, removed the cooling bath and stirred for one additional hour. The mixture was diluted with DCM, extracted with bleach/water, 1 M citric acid, water, dried (Na2SO4), concentrated.

Workup

  1. stirringAfter stirring for 10 min
  2. stirringstirred one hour
  3. customremoved the cooling bath
  4. stirringstirred for one additional hour
  5. additionThe mixture was diluted with DCM
  6. extractionextracted with bleach/water, 1 M citric acid, water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-00fb0c41b55a48629f49e5a6b0fc6544
Source dataset
uspto-grants-2013_03
Patent number
US08394819B2

Reaction notes

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