2-Methoxybenzoic acid → 5-Bromo-2-methoxybenzoic acid

To a solution of 2-methoxybenzoic acid (6 g, 39.4 mmol) in 80 mL of acetonitrile was added N-bromosuccinimide (7.4 g, 41.4 mmol) in 20 mL of acetonitrile. The reaction mixture was warmed to ambient temperature and the mixture was allowed to stir for 16 hours. Additional N-bromosuccinimide (14.8 g, 82.8 mmol) was added and the reaction mixture stirred for an additional 48 hours. The mixture was quenched with 25 mL of H2O and the layers were separated. The aqueous layer was extracted with three 15 mL of portions of CH2Cl2 and the combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via column chromatography (SiO2, 50% hexanes in ethyl acetate) afforded the title compound. MS (DCI/NH3) m/z 248, 250 (M+NH4)+.

1. stirringthe reaction mixture stirred for an additional 48 hours
2. customThe mixture was quenched with 25 mL of H2O
3. customthe layers were separated
4. extractionThe aqueous layer was extracted with three 15 mL of portions of CH2Cl2
5. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customPurification via column chromatography (SiO2, 50% hexanes in ethyl acetate)

ORD record

ord-33cf17b0582845fca427e819429703db

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08546583B2