Methyl morpholine oxide → Methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate

HRID 1368812Notes

Reaction equation

HRID 1368812 reaction equation
Br[CH2:2][C:3]1[C:4]([Cl:17])=[C:5]([CH:10]=[CH:11][C:12]=1[S:13]([CH3:16])(=[O:15])=[O:14])[C:6]([O:8][CH3:9])=[O:7].C[N+]1([O-])CC[O:22]CC1>C(#N)C>[Cl:17][C:4]1[C:3]([CH:2]=[O:22])=[C:12]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

4

Reactant 2

HCID 82029Methyl morpholine oxideHCID 10969914Methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate

Product 1

HCID 18517410Methyl 2-chloro-3-formyl-4-methylsulfonylbenzoateYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 41.0 g (0.12 mol) of methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate in 250 ml of acetonitrile was admixed with 42.1 g (0.36 mol) of N-methylmorpholine N-oxide. The reaction mixture was stirred for 12 hours at room temperature and then concentrated, and the residue was taken up in ethyl acetate. The solution was extracted with water, dried with sodium sulfate and concentrated. 31.2 g (94% of theory) of methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate were obtained.

Workup

  1. concentrationconcentrated
  2. extractionThe solution was extracted with water
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e496e1b894fd4f1ab4ca1ca0bab1ffad
Source dataset
uspto-grants-2003_06
Patent number
US06576596B1

Reaction notes

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