Methanol → Methyl 4-bromo-2,5-difluorobenzoate

HRID 452461

Reaction equation

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

Participants

Reactant 2

HCID 887Methanol

HCID 8228574-Bromo-2,5-difluorobenzoic acid

Product 1

HCID 66887346Methyl 4-bromo-2,5-difluorobenzoate

Procedure

4-bromo-2,5-difluorobenzoic acid (4.82 g, 20.3 mmol) and methanol (100 ml, saturated with gaseous HCl) was heated at 65° C. for 3 h. The volatiles were evaporated, MeOH was added and once again it was evaporated. This procedure was repeated three times. Purification by flash column chromatography (isooctane/EtOAc 4:1) gave the title compound (4.2 g). MS m/z (rel. intensity, 70 eV) 252 (M+, 33), 250 (M+, 34), 221 (95), 219 (bp), 193 (20), 191 (21), 112 (32).

Workup

customThe volatiles were evaporated
additionMeOH was added
customonce again it was evaporated
customPurification by flash column chromatography (isooctane/EtOAc 4:1)

Sources & evidence

ORD record: ord-e7d8122d4d2541f782692e9081313de3
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492372B2

Linked notes

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