Hydrogen Bromide → HCID 59186000, compound

Participants

Reaction Steps

1-(6-Chloro-4-methyl-pyridin-3-yl)-propan-1-one (100 mg, 0.545 mmol) is dissolved in hydrobromic acid (48%) (2 ml, 17.68 mmol); to this is then added bromine (0.031 ml, 0.599 mmol) dropwise and the resulting orange solution stirred at RT. After 4 hours, further 0.2 eq (5 ul) of bromine is added and the reaction is left stirring O/N at RT. The reaction mixture is basified by careful addition of 2M Na2CO3 (5 ml) and then extracted into EtOAc (2×25 ml). The combined organic phase is washed with H2O, brine, dried (MgSO4) and evaporated to give a clear oil. The crude material is chromatographed on silica gel (20 g) eluting with (10% EtOAc/iso-hexane) to give the desired compound; MS: m/z 262.1 [M+H]+; 1H NMR (400 MHz, (CDCl3) δ 7.9 (d, 1H), 7.3 (d, 1H), 5.1 (q, 1H), 2.7 (s, 3H), 1.9 (d, 3H).

Provenance & Evidence