Methanol → Methyl 4-chloro-3-(methylsulfonyl)benzoate

HRID 219829Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[S:11]([CH3:14])(=[O:13])=[O:12].S(Cl)(Cl)=O.[CH3:19]O>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:19])=[O:7])=[CH:4][C:3]=1[S:11]([CH3:14])(=[O:12])=[O:13]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 1826704-Chloro-3-methanesulfonylbenzoic acid

Product 1

HCID 10490815Methyl 4-chloro-3-(methylsulfonyl)benzoate

Conditions

Temperature: 0 °C

Procedure

4-chloro-3-(methylsulfonyl)benzoic acid (Enamine, 500 mg; 2.13 mmol; 1 eq.) was dissolved in MeOH (10 mL) The solution was cooled down to 0° C. Thionyl chloride (0.62 mL; 8.52 mmol; 4 eq.) was added dropwise.

Sources & evidence

ORD record: ord-d51a0ee0e54e4df4aaae02a934a574d4
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202865B2

Reaction notes

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