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

HRID 1276110Notes

Reaction equation

HRID 1276110 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 was stirred at room temperature for 12 hours and then concentrated and the residue was taken up in ethyl acetate. The solution was washed with water, dried and concentrated. 31.2 g (94% of theory) of methyl 2-chloro-3-formyl-4-methylsulfonylbenzoate were obtained.

Workup

  1. concentrationconcentrated
  2. washThe solution was washed with water
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fe937c02f28745358b2e3cf0e8087dbd
Source dataset
uspto-grants-2000_12
Patent number
US06165944

Reaction notes

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