Toluene → HCID 86715129, compound

To a solution of 3-bromo-2-fluorobenzoic acid (15 g) in toluene (200 mL) was added SOCl2 (12.2 g) at r.t. and the suspension was heated to reflux with stirring for 2.5 h. The volatiles were removed under reduced pressure. The residue was taken up in DCM (20 mL) and added to a solution of AlCl3 (9.1 g) in dichloroethane at 10-20° C. Ethylene was bubbled through the solution for 4 hours after which the resulting mixture was stirred for 15 hours and then quenched with 4 N HCl (100 mL). The resulting layers were separated and the aqueous phase was extracted with DCM (100 mL×3). The combined organic layers were washed with water (50 mL×3), brine (50 mL) and dried over Na2SO4. After filtration, the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: DCM/PE 1:200) to provide the subtitle compound. MS ESI+: m/z=265 [M+H]+.

1. temperaturethe suspension was heated
2. temperatureto reflux
3. customThe volatiles were removed under reduced pressure
4. additionadded to a solution of AlCl3 (9.1 g) in dichloroethane at 10-20° C
5. customEthylene was bubbled through the solution for 4 hours after which the resulting mixture
6. stirringwas stirred for 15 hours
7. customquenched with 4 N HCl (100 mL)
8. customThe resulting layers were separated
9. extractionthe aqueous phase was extracted with DCM (100 mL×3)
10. washThe combined organic layers were washed with water (50 mL×3), brine (50 mL)
11. dry with materialdried over Na2SO4
12. filtrationAfter filtration
13. customthe solvent was removed under reduced pressure
14. customThe residue was purified by column chromatography on silica gel (eluent: DCM/PE 1:200)

ORD record

ord-7cde63efaf7145f1bd883c0a8673aab2

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08853412B2