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ChemicalBook CAS DataBase List 5-amino-2-bromo-4-methylbenzoic acid
745048-63-9

5-amino-2-bromo-4-methylbenzoic acid synthesis

3synthesis methods
-

Yield: 100%

Reaction Conditions:

with N-Bromosuccinimide in N,N-dimethyl-formamide at 5 - 15; for 1.08 h;Inert atmosphere;

Steps:

1 Intermediate 1: 5-amino-2-bromo-4-methylbenzoic acid
NBS (11.87 g, 66.15 mmol) was added portionwise to 3-amino-4-methylbenzoic acid (10.00 g,10 66.15 mmol) in DMF (50 mL) at 5°C over a period of5 minutes so that the temperature did not riseabove 15°C. The resulting solution was stirred at 5°C for 1 h. The reaction mixture was poured onto ice water (250 mL) with stirring. The resulting solid was filtered, washed with ice cold water anddried to afford the title compound (15.21 g, 100%) as a pale pink solid; 1H NMR (400 MHz,DMSO) 2.04- 2.09 (3H, m), 5.21 (2H, s), 7.06 (lH, s), 7.21 (lH, d), 12.84 (lH, s).

References:

ASTRAZENECA AB;CANCER RESEARCH TECHNOLOGY LIMITED;FINLAY, Maurice, Raymond, Verschoyle;GOLDBERG, Frederick, Woolf;HOWARD, Martin, Richard;TING, Attilla, Kuan, Tsuei WO2019/238929, 2019, A1 Location in patent:Page/Page column 39; 43