3-Bromo-5-methylbenzaldehyde oxime synthesis

Yield:1205515-03-2 91%

Reaction Conditions:

with hydroxylamine hydrochloride in ethanol; for 2 h;Reflux;

Steps:

12

3-Bromo-5-methylbenzaldehyde oxime{2); To a stirred solution of hydroxylamine hydrochloride^. Og₅ 101mmol) and triethy. amine(16.6mi, 1 19mmol) in ethanoi(150ml), was added 3-bromo-5- methylbenzaldehyde(18.3g, 92mmoi). The mixture was then heated to reflux for 2hr. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane, washed with water, dried with MgSO₄, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography(eluent, ethyl acetate hexane(1 14)) to afford 18g(91%) of the title compound as a white solid m p 128-129°C¹H-NMR(200MHz, CDCI₃) δ 2 34(3H, s), 7 30(1H₁ s), 7 35(1 H, s), 7 53(1 H, S)₁ 7 66(1 H s), 8 04(br s)

References:

WO2010/9047,2010,A1 Location in patent:Page/Page column 84-85