Azobisisobutyronitrile → Methyl 2-bromo-2-(2-chloro-4-fluorophenyl)acetate

Temperature

80 °C

Methyl 2-chloro-4-fluorophenylacetate (3.15 g, 15.6 mmol), N-bromosuccinimide (2.77 g, 15.6 mmol) and AIBN (255 mg, 1.56 mmol) were suspended in benzene (50.0 mL) and degassed via N2 stream. The resulting mixture was heated to 80° C. for 12 h. After cooling to rt, the mixture was partially concentrated in vacuo and partitioned between ether and water. The layers were separated, and the organic layer was washed with water and brine. The organics were dried (MgSO4), filtered and concentrated in vacuo. The resulting crude oil was purified by flash chromatography on silica gel (gradient elution; 0%-20% EtOAc/hexanes as eluent) to afford the title compound i-1a. 1HNMR (500 MHz, CDCl3): δ 7.82 (dd, 1H, J=6.0, 8.8 Hz), 7.17 (dd, 1H, J=2.6, 8.3 Hz), 7.08 (m, 1H), 5.88 (s, 1H), 3.84 (s, 3H).

1. customdegassed via N2 stream
2. temperatureAfter cooling to rt
3. concentrationthe mixture was partially concentrated in vacuo
4. custompartitioned between ether and water
5. customThe layers were separated
6. washthe organic layer was washed with water and brine
7. dry with materialThe organics were dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe resulting crude oil was purified by flash chromatography on silica gel (gradient elution; 0%-20% EtOAc/hexanes as eluent)

ORD record

ord-6984ff285dc6409493e984ec98b9f4bb

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08933113B2