Bromoacetyl bromide → 2-bromo-N-(2-chloro-5-cyano-3-nitrophenyl)acetamide

Participants

Reaction Conditions

Reaction Steps

To the solution of 3-amino-4-chloro-5-nitrobenzonitrile (300 mg, 1.518 mmol) in DCM (10 mL) at 0° C. was added TEA (0.317 mL, 2.278 mmol) and then 2-bromoacetyl bromide (0.145 mL, 1.670 mmol) was added drop wise. The reaction mixture was stirred at 0° C. for 3 h. LC-MS indicated a new peak. Then it was diluted with DCM and saturated aqueous sodium bicarbonate solution was added. After separating the layers, the aqueous layer was further extracted with DCM. The combined organic extracts were washed with water, brine, dried over MgSO4, filtered and concentrated. The crude was used in the next step without purification. To a solution of above obtained crude 2-bromo-N-(2-chloro-5-cyano-3-nitrophenyl)acetamide (500 mg, 1.570 mmol) in DCM (4 mL) was added TEA (0.438 mL, 3.14 mmol) then a solution of 2-(methylamino)ethanol (118 mg, 1.570 mmol) in THF (4 mL) was added slowly. After stirring at room temperature for 1 h, LC-MS indicated completion. After concentration purification via flash chromatography (0-5% MeOH in DCM, 12 g) gave N-(2-chloro-5-cyano-3-nitrophenyl)-2-((2-hydroxyethyl)(methyl)amino)acetamide (170 mg) as a yellow oil, MS (ESI+) m/z 313.0

Provenance & Evidence