4-Bromoanisole → HCID 60209035, compound

Temperature

0 °C

3-Fluorophenylacetic acid (4.90 g, 32.07 mmoles) was dissolved in 50 ml dichloromethane. To this mixture, oxalylchloride (3.5 ml, 40.08 mmoles) and DMF (3 drops) were added at 0° C. and stirred for 30 min. The solvent was evaporated and dissolved in 50 ml dichloromethane. To this mixture, 4-bromoanisole (5.0 g, 26.72 mmoles) was added and cooled to 0° C. At 0° C. AlCl3 (5.3 g, 40.08 mmoles) was added and the reaction mixture was warmed to RT and stirred for 12 h. The reaction mixture was quenched by the addition of 2N HCl, extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as off-white solid (6.6 g, 80% yield. 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 12.02(s,1H), 7.94(d, J=2.4Hz, 1H), 7.57(dd, J=8.9,2.4.1Hz, 1H), 7.36(m,1H), 7.04(m, 3H), 6.90(d, J=8.9 Hz, 1H),4.28(s, 2H).

1. customThe solvent was evaporated
2. dissolutiondissolved in 50 ml dichloromethane
3. customAt 0° C
4. temperaturethe reaction mixture was warmed to RT
5. stirringstirred for 12 h
6. customThe reaction mixture was quenched by the addition of 2N HCl
7. extractionextracted with ethyl acetate
8. dry with materialdried over sodium sulphate
9. concentrationconcentrated
10. customThe crude product was purified by column chromatography with ethyl acetate

ORD record

ord-8bfe4decdd994be28d1454f72fd08bcd

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018375B2