Bromoacetyl bromide → HCID 18929214, compound

Participants

Reaction Steps

To a solution of 2-amino-5-bromobenzoic acid (11.2 g, 0.052 mol) in anhydrous DMF (40 mL) and anhydrous dioxane (40 mL) was added, dropwise, bromoacetyl bromide while keeping the internal temperature between 0° C. and 5° C. After the addition was completed (~25 min), the ice-bath was removed and the mixture was stirred for 20 h at rt. The reaction mixture was cooled in an ice-bath, water was added (100 mL), and then the mixture was poured into ice water. The precipitate which formed was filtered, washed with water, and then dried in a vacuum oven for 20 h at 40°-45° C., affording 9.9 g (57%) of the title compound: mp 203°-204° C.; 1H NMR (CDCl3) δ11.67 (s, 1H, NH), 8.64 (d, 1H, J=8.8), 8.55 (d, 1H, J=2.4), 7.71 (dd, 1H, J=2, J=6.8), 3.72 (s, 2H ); 13C NMR (CDCl3): 200.55, 138.06, 134.22, 134.20, 122.06, 107.46. 67.08; MS (EI, m/z) 337 (M+). HRMS (EI) calcd for C9H7NO3Br2 334.8792, found 334.8791.

Provenance & Evidence