Carbon Dioxide → 3-Bromo-2-fluorobenzoic acid

To a solution of 1-bromo-2-fluorobenzene (6.0 g, 34.3 mmol) in dry tetrahydrofuran (50 ml) under nitrogen, at −78° C. was added lithium diisopropylamide (2.5 M in hexane, 18.8 ml, 37.7 mmol). The mixture was stirred for 50 minutes and then poured onto crushed solid carbon dioxide. The reaction mixture was brought to ambient temperature and aqueous sodium carbonate (10%, 50 ml) was added. The aqueous phase was washed with diethyl ether (2×100 ml), and then made acidic by addition of aqueous hydrochloric acid. The acidified aqueous phase was extracted with ethyl acetate (2×50 ml) and the combined organic phases was dried (MgSO4) and evaporated to dryness to give the title compound (4.24 g).

1. additionpoured
2. customwas brought to ambient temperature
3. washThe aqueous phase was washed with diethyl ether (2×100 ml)
4. additionmade acidic by addition of aqueous hydrochloric acid
5. extractionThe acidified aqueous phase was extracted with ethyl acetate (2×50 ml)
6. dry with materialthe combined organic phases was dried (MgSO4)
7. customevaporated to dryness

ORD record

ord-80f18dcb22634f1080bad182417be749

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08314126B2