Sodium Methoxide → HCID 15132841, compound

HRID 1682147Notes

Reaction equation

HRID 1682147 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].[CH3:18][O-:19].[Na+]>CO>[Cl:17][C:4]1[C:3]([CH2:2][O:19][CH3:18])=[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 10942334Sodium MethoxideHCID 10969914Methyl 3-bromomethyl-2-chloro-4-methylsulfonylbenzoate

Product 1

HCID 15132841HCID 15132841, compoundYield 103.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution comprising 12.0 g of methyl 3-bromomethyl-2-chloro-4-methanesulfonylbenzoate prepared in Reference Example 3(1) and 100 ml of methanol, 50 ml of a methanol solution containing 1.7 g of sodium methoxide was added, and the mixture was stirred at room temperature overnight. The solvent was distilled off under reduced pressure. Then, dilute hydrochloric acid was added to the residue, and the mixture was extracted with chloroform. The extract was washed with water and dried over anhydrous sodium sulfate. Then, the solvent was distilled off to obtain 9.5 g of the desired product as a crude product. The crude product was purified by silica gel column chromatography (eluted with benzene) to obtain 7.5 g of a purified product as an oily substance.

Workup

  1. additionwas added
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionThen, dilute hydrochloric acid was added to the residue
  4. extractionthe mixture was extracted with chloroform
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-25892c250a044d018a5a09c86c23da32
Source dataset
uspto-grants-1992_12
Patent number
US05175299

Reaction notes

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