Dimethyl Sulfoxide → 5-Bromo-2-chlorobenzaldehyde

HRID 1441957Notes

Reaction equation

HRID 1441957 reaction equation
CS(C)=O.ClCCl.C(Cl)(=O)C(Cl)=O.[Br:14][C:15]1[CH:16]=[CH:17][C:18]([Cl:23])=[C:19]([CH2:21][OH:22])[CH:20]=1>C(Cl)(Cl)Cl.O.C(N(CC)CC)C>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([Cl:23])=[C:19]([CH:20]=1)[CH:21]=[O:22]

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 5074766(5-Bromo-2-chlorophenyl)methanol

Product 1

HCID 106089255-Bromo-2-chlorobenzaldehyde

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

18 ml (0.26 mol) of DMSO are introduced into 64 ml of dichloromethane and, at −78° C., 16.1 g (0.127 mol, 11.1 ml) of oxalyl chloride are added. After 30 min, a solution of 13.1 g (59 mmol) of (5-bromo-2-chlorophenyl)methanol in 100 ml of chloroform is added dropwise. After 20 min, 40 ml of triethylamine are added and the reaction mixture is slowly warmed to RT. After the addition of 50 ml of water the mixture is extracted several times with ethyl acetate. The combined organic phases are washed successively with 2N hydrochloric acid, water, a saturated sodium bicarbonate solution and a saturated sodium chloride solution. The organic phase is dried over magnesium sulfate and concentrated in vacuo. The resulting solid is dried Yunder high vacuum to constant weight.

Workup

  1. waitAfter 20 min
  2. extractionis extracted several times with ethyl acetate
  3. washThe combined organic phases are washed successively with 2N hydrochloric acid, water
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resulting solid is dried Yunder high vacuum to constant weight

Sources & evidence

ORD record
ord-80091e32efc74464b4882df190f1e7c2
Source dataset
uspto-grants-2010_02
Patent number
US07655643B2

Reaction notes

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