Methanol → Methyl 4-bromo-3-(trifluoromethyl)benzoate

HRID 1950821Notes

Reaction equation

S(Cl)(Cl)=O.[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]=1[C:15]([F:18])([F:17])[F:16].[CH3:19]O>>[Br:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([O:12][CH3:19])=[O:11])=[CH:8][C:7]=1[C:15]([F:16])([F:17])[F:18]

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 247213904-Bromo-3-(trifluoromethyl)benzoic acid

Product 1

HCID 10891333Methyl 4-bromo-3-(trifluoromethyl)benzoate

Procedure

Thionyl chloride (16.2 mL; 223 mmol; 4 eq.) was added to a suspension of 4-bromo-3-(trifluoromethyl)benzoic acid (15 g; 55.8 mmol; 1 eq.) in MeOH (300 mL) and the reaction mixture was stirred at room temperature for 16 hours.

Sources & evidence

ORD record: ord-d216935a9da74f4191aaaa111d0fff38
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08404676B2

Reaction notes

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