Hydrochloric Acid → HCID 28457253, compound

To a solution of crude N-(3-bromophenyl)-2-phenylacetamide (3.02 g, 10.4 mmol) in dry tetrahydrofuran (25 mL) was added 1.0 N borane-tetrahydrofuran complex (1:1. 26 mL, 26.12 mmol) from an addition funnel at 0° C. The reaction was refluxed under nitrogen overnight. Reaction mixture was cooled to room temperature, treated with 2.0 N aqueous sodium hydroxide (30 mL) and then stirred for 20 min. The reaction was then cooled again at 0° C. and neutralized with 2.0 N aqueous hydrochloric acid (60 mL) and further stirred for 30 min. The aqueous layer was extracted with ethyl acetate (3×100 mL). The organic layer was washed with water (20 mL), saturated aqueous sodium chloride (50 mL), dried over magnesium sulfate, filtered, and concentrated to afford 3-Bromo-N-(2-phenylethyl)aniline (2.55 g, 85% yield) as brown oil with reasonable purity: 1H NMR (400 MHz, CDCl3): 7.30 (t, 2H), 7.20 (m, 3H), 6.95 (t, 1H), 6.78 (br d, 1H), 6.70 (t, 1H), 6.45 (dd, 1H), 3.62 (br s, 1H), 3.40 (m, 2H), 2.92 (t, 2H); MS (EI) for C14H12NOBr: 290 MH+).

1. temperatureThe reaction was refluxed under nitrogen overnight
2. customReaction mixture
3. stirringfurther stirred for 30 min
4. extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
5. washThe organic layer was washed with water (20 mL), saturated aqueous sodium chloride (50 mL)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-80fd6c348f1745e8b81a184ad50a21f5

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07704995B2