[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[Cl:10])[C:5]#[N:6].[Br:14][CH2:15][C:16](Br)=[O:17]>C(Cl)Cl.C(=O)(O)[O-].[Na+]>[Br:14][CH2:15][C:16]([NH:1][C:2]1[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]=1[Cl:10])=[O:17]To the solution of 3-amino-4-chloro-5-nitrobenzonitrile (300 mg, 1.518 mmol) in DCM (12 mL) at 0° C. was added TEA (0.635 mL, 4.56 mmol) and then 2-bromoacetyl bromide (0.291 mL, 3.34 mmol) was added drop wise. The reaction mixture was stirred at 0° C. for 1 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. Purification via flash chromatography (0-70% EtOAc in DCM, 40 g) gave 2-bromo-N-(2-chloro-5-cyano-3-nitrophenyl)acetamide (400 mg) as a light yellow solid.
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