Water → Methyl 5-bromo-3-chloro-2-hydroxy-4-(trifluoromethyl)benzoate

HRID 629357Notes

Reaction equation

[Cl:1][C:2]1[C:3]([OH:16])=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[C:5]([O:7][CH3:8])=[O:6].[Br:17]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:17][C:10]1[C:11]([C:12]([F:14])([F:15])[F:13])=[C:2]([Cl:1])[C:3]([OH:16])=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

Conditions

Temperature: 15 °C

Procedure

To a solution of methyl 3-chloro-2-hydroxy-4-(trifluoromethyl)benzoate (6.30 g) in DMF (65.0 mL) was added N-bromosuccinimide (4.41 g), and the mixture was stirred at 15° C. for 16 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (7.00 g).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-e3f3c47a277c43b4bc0cbd5465f0b5c0
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09315458B2

Reaction notes

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