Water → 4-Bromo-3-methylbenzaldehyde oxime

To a solution of 4-bromo-3-methyl-benzaldehyde (4.3 g) (Example I1) in ethanol (50 ml), were added at ambient temperature hydroxylamine hydrochloride (1.75 g), sodium acetate (2.07 g) and water (15 ml). The reaction mixture was stirred at ambient temperature for 3 hours. The reaction mixture was concentrated and the residue diluted with ethyl acetate and aqueous sodium hydroxide (2M). The phases were separated and the organic phase was washed with brine, dried over sodium sulfate, and concentrated. The residue was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 4:1) to give 4-bromo-3-methyl-benzaldehyde oxime (3.65 g) as a white solid. 1H-NMR (400 MHz, CDCl3): 8.05 (s, 1H), 7.50 (m, 2H), 7.25 (d, 1H), 2.40 (s, 3H) ppm.

1. customwere added at ambient temperature
2. concentrationThe reaction mixture was concentrated
3. additionthe residue diluted with ethyl acetate and aqueous sodium hydroxide (2M)
4. customThe phases were separated
5. washthe organic phase was washed with brine
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated
8. customThe residue was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate 4:1)

ORD record

ord-dd065fadc7b64c448ffb011648dc18da

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08623896B2