Dimethylformamide → 3-(2-Methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl chloride

HRID 1257988Notes

Reaction equation

HRID 1257988 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([CH3:19])=[C:8]([CH:12]=[CH:13][C:14]=1[S:15]([CH3:18])(=[O:17])=[O:16])[C:9](O)=[O:10].C(Cl)(=O)C([Cl:23])=O.CN(C=O)C>C(Cl)(Cl)Cl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([CH3:19])=[C:8]([CH:12]=[CH:13][C:14]=1[S:15]([CH3:18])(=[O:17])=[O:16])[C:9]([Cl:23])=[O:10]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 667565243-(2-Methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid

Product 1

HCID 866548323-(2-Methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl chlorideYield 97.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-(2-Methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid (500 mg) was dissolved in chloroform (20 mL), and oxalyl chloride (500 mg) and a catalytic amount of DMF were added, followed by stirring at room temperature for 3 hours. Under reduced pressure, the solvent and an excess reagent were distilled off to obtain 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoyl chloride (520 mg) as an oily product.

Workup

  1. distillationUnder reduced pressure, the solvent and an excess reagent were distilled off

Sources & evidence

ORD record
ord-c074bbf761974e4a93545a977a7ec73d
Source dataset
uspto-grants-2013_06
Patent number
US08466089B2

Reaction notes

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