ChemicalBook CAS DataBase List tert-Butyl N-[5-bromo-2-chlorophenyl]carbamate

tert-Butyl N-[5-bromo-2-chlorophenyl]carbamate synthesis

6synthesis methods

Product Name:tert-Butyl N-[5-bromo-2-chlorophenyl]carbamate
CAS Number:740806-51-3
Molecular formula:C11H13BrClNO2
Molecular Weight:306.58

24424-99-5 Synthesis

24424-99-5
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60811-17-8
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tert-Butyl N-[5-bromo-2-chlorophenyl]carbamate

740806-51-3
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Yield:740806-51-3 97%

Reaction Conditions:

with dmap;triethylamine in dichloromethane at 0 - 20;

Steps:

R1

Step Rl: To 5-bromo-2-chloroaniline (2.917 g, 14.13 mmol) in DCM (15 mL) was added triethylamine (5.91 mL, 42.4 mmol). The reaction was cooled to 0 °C, and di-tert-butyl dicarbonate (3.94 mL, 16.95 mmol) was added. The reaction was warmed to ambient temp., and DMAP (1.726 g, 14.13 mmol) was added. Violent bubbling and precipitate were observed within one minute. The reaction mixture was stirred at RT for 16 hours. The product was purified by flash chromatography (DCM/Hexanes 1 : 1, R 0.61) to give 4.21 g (97% yield). ^XH-NMR (CDC1₃, 400 MHz): δ 8.43 (1H, d, J= 2.0 Hz), 7.19 (1H, d, J= 8.5 Hz), 7.09 (1H, dd, Jl = 8.5 Hz, J2 = 2.5 Hz), 6.99 (1H, s), 1.55 (9H, s).

References:

WO2012/33736,2012,A1 Location in patent:Page/Page column 49-50

21739-92-4 Synthesis