Sodium Hydroxide → 4-Bromo-3-chloro-2-methylaniline

A solution of N-(4-bromo-3-chloro-2-methyl-phenyl)-acetamide (3.37 g, 12.80 mmol) in H2SO4: H2O (1:1) was refluxed for 3 hours. The reaction mixture was cooled to room temperature and neutralized with NaOH and extracted with Et2O (3×150 mL). The combined organic phases were washed with H2O (3×100 mL) and brine (1×100 mL), then dried over MgSO4 and concentrated. Purification by column chromatography using hex:EtOAc (4:1) as the eluant afforded the title aniline. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ 2.31 (s, 3H), 3.93 (br s, 2H), 6.47 (d, J=8.79 Hz, 1H), 7.24 (d, J=7.91 Hz, 1H).

1. extractionextracted with Et2O (3×150 mL)
2. washThe combined organic phases were washed with H2O (3×100 mL) and brine (1×100 mL)
3. dry with materialdried over MgSO4
4. concentrationconcentrated
5. customPurification by column chromatography

ORD record

ord-e956ed13305c48259b6e0bd74dc076a1

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08557853B2