Hydrochloric Acid → 3-Bromo-5-fluoroaniline

Temperature

100 °C

To a solution of N-(3-bromo-5-fluorophenyl)acetamide (Intermediate 181, 8.7 g, 37.4 mmol) in ethanol (30 mL) was added concentrated hydrochloric acid (80 mL). The reaction was heated to 100° C. for 1 hr. It was cooled to room temperature and neutralized with 5N sodium hydroxide. The crude product was extracted with ethyl acetate (2×100 mL), the combined organic layers were washed with brine, dried over magnesium sulfate, filtered, and concentrated to dryness. Chromatography on silica gel with a gradient of 5-10% ethyl acetate in hexanes gave 5.3 g (75%) of the product as a yellow oil.

1. extractionThe crude product was extracted with ethyl acetate (2×100 mL)
2. washthe combined organic layers were washed with brine
3. dry with materialdried over magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated to dryness

ORD record

ord-3c3c87c6274d4482ab6aeb8f4ce5955e

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08124602B2