Methanol → HCID 20577071, compound

Reaction equation

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

Participants

Reactant 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 185485832-Bromo-5-fluoro-3-nitrobenzoic acid

Product 1

HCID 20577071HCID 20577071, compoundYield 84%

Conditions

Temperature: 65 °C

Procedure

To the solution of 2-bromo-5-fluoro-3-nitrobenzoic acid (35 g) in MeOH (400 mL) was added SOCl2 (40 mL) drop-wise at 10-15° C. The reaction was then stirred at 65° C. for 1 h. After cooling to room temperature, the solvent was evaporated in vacuum to afford a residue, which was chromatographed on silica gel using gradient eluant of 0-100% EtOAc in hexane to provide methyl 2-bromo-5-fluoro-3-nitrobenzoate (20 g, 84%).

Workup

temperatureAfter cooling to room temperature
customthe solvent was evaporated in vacuum
customto afford a residue, which
customwas chromatographed on silica gel using gradient eluant of 0-100% EtOAc in hexane

Sources & evidence

ORD record: ord-67a2b8a66da548e8acde762fba7b729a
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09328111B2

Reaction notes

Loading…