Hexachloroethane → 2-Chloro-3-fluorobenzoic acid

Temperature

-90 °C

A solution of 3-fluorobenzoic acid (4.02 g, 28.71 mmol) in 20 mL of THF was added dropwise to a suspension of TMEDA (10.00 mL, 66.3 mmol) and 1.3M sec-BuLi (48 mL, 62.4 mmol) in 50 mL of THF at −90° C. The mixture was stirred at −90° C. for 35 min. The mixture was warmed to −78° C. when a solution of hexachloroethane (27.0 g, 113.9 mmol) in 50 mL of THF was added. After 20 h, the reaction was quenched with water and diluted with diethyl ether. The bilayer was adjusted to pH ˜1-2 with conc. HCl. The organic layer was washed with water, brine, dried and concentrated to give 30.4 g crude as a tan solid, which was washed with hexane to give 3.728 g (74%) of the desired product 1a (light tan solid). MS (m/z) 175.2 (M+H).

1. additionwas added
2. waitAfter 20 h
3. customthe reaction was quenched with water
4. additiondiluted with diethyl ether
5. washThe organic layer was washed with water, brine
6. customdried
7. concentrationconcentrated
8. customto give 30.4 g crude as a tan solid, which
9. washwas washed with hexane

ORD record

ord-f150cd30123a4ab5a7dffe44ee29c07b

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709485B2