ChemicalBook CAS DataBase List 2-BROMO-3-CHLOROANILINE

2-BROMO-3-CHLOROANILINE synthesis

7synthesis methods

Product Name:2-BROMO-3-CHLOROANILINE
CAS Number:96558-73-5
Molecular formula:C6H5BrClN
Molecular Weight:206.47

Carbamic acid, N-(2-bromo-3-chlorophenyl)-, 1,1-dimethylethyl ester

1463053-89-5

96558-73-5

Step B: Synthesis of 2-bromo-3-chloroaniline To a solution of tert-butyl (2-bromo-3-chlorophenyl)carbamate (0.4 g) in dichloromethane (DCM, 20 mL) was added trifluoroacetic acid (TFA, 10 mL). The reaction mixture was stirred at room temperature for 3 h. The reaction solution was subsequently concentrated by rotary evaporator. Water (10 mL) was added to the concentrated residue and the mixture was extracted with dichloromethane (2 x 20 mL). The organic phase was separated and washed sequentially with saturated aqueous sodium bicarbonate (NaHCO3) and saturated aqueous sodium chloride (NaCl), dried over anhydrous sodium sulfate (Na2SO4), and then the organic phase was concentrated to give the title compound 2-bromo-3-chloroaniline as a solid (0.2 g, 77% yield). 1H NMR (400 MHz, CDCl3) δ 7.03-6.99 (1H, m), 6.85-6.83 (1H, d, J = 8.0 Hz), 6.65-6.63 (1H, d, J = 8.0 Hz), 4.25 (2H, s).

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Yield:96558-73-5 77%

Reaction Conditions:

with trifluoroacetic acid in dichloromethane at 20; for 3 h;

Steps:

11.B Step B: 2-bromo-3-chloroaniline
Step B: 2-bromo-3-chloroaniline [0186] To tert-butyl (2-bromo-3-chlorophenyl)carbamate (0.4 g) in DCM (20 mL) was added TFA (10 mL). The reaction mixture was stirred at RT for 3 hours and then concentrated. Water (10 mL) was added to the residue, and the mixture was extracted with DCM (2 x 20 mL). The organic phase was separated, washed with aqueous saturated NaHC0₃ and saturated NaCl, dried over anhydrous Na₂S0₄, and concentrated to give the title compound as a solid (0.2 g, 77%). 1H NMR (400 MHz, CDC1₃) δ 7.03-6.99 (IH, m), 6.85- 6.83 (IH, d, J=8.0 Hz), 6.65-6.63 (IH, d, J=8.0 Hz), 4.25 (2H, s).

References:

TAKEDA PHARMACEUTICAL COMPANY LIMITED;LAWSON, John David;SABAT, Mark;SMITH, Christopher;WANG, Haixia;CHEN, Young K.;KANOUNI, Toufike WO2013/148603, 2013, A1 Location in patent:Paragraph 0185-0186

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