Dichloromethane → Benzoic acid, 4-(bromomethyl)-2,5-difluoro-, methyl ester

HRID 512032Notes

Reaction equation

[F:1][C:2]1[CH:11]=[C:10]([CH3:12])[C:9]([F:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:14]N1C(=O)CCC1=O.ClCCl>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:14][CH2:12][C:10]1[C:9]([F:13])=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([F:1])[CH:11]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A solution of methyl 2,5-difluoro-4-methylbenzoate (Preparation 2, 500 mg, 2.69 mmol), N-bromosuccinimide (526 mg, 2.96 mmol) and dibenzoyl peroxide (20 mg, 0.08 mmol) dissolved in carbon tetrachloride (10 mL) was heated to reflux at 85° C. for 18 hours. The mixture was cooled to room temperature, dichloromethane (20 mL) added and the mixture poured into a separating funnel. The resulting organic layer was separated and washed successively with water (20 mL) and aqueous sodium thiosulphate solution (20 mL). The organic layer was dried over magnesium sulphate and filtered. The solvent was removed under reduced pressure to give an oil (748 mg). The crude product was purified by flash column chromatography (Biotage™ 50 g silica cartridge) eluting with 10% ethyl acetate in heptane to give the title compound (479 mg, 67%) as an oil.

Workup

temperaturewas heated
temperatureThe mixture was cooled to room temperature
additionthe mixture poured into a separating funnel
customThe resulting organic layer was separated
washwashed successively with water (20 mL) and aqueous sodium thiosulphate solution (20 mL)
dry with materialThe organic layer was dried over magnesium sulphate
filtrationfiltered
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-12c8ba83e237485ea6b9e9e68da632af
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102621B2

Reaction notes

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