[1-(4-BROMO-PHENYL)-ETHYL]-CARBAMIC ACID TERT-BUTYL ESTER Chemical Properties

Boiling point:

383.1±25.0 °C(Predicted)

Density 

1.282±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

pka

11.94±0.46(Predicted)

Appearance

White to off-white Solid

[1-(4-BROMO-PHENYL)-ETHYL]-CARBAMIC ACID TERT-BUTYL ESTER Usage And Synthesis

Synthesis

General procedure for the synthesis of tert-butyl (1-(4-bromophenyl)ethyl)carbamate from di-tert-butyl dicarbonate and 1-(4-bromophenyl)ethylamine (refer to Example 5): synthesis of 1-bromo-4-(1-tert-butoxycarbonylaminoethyl)benzene (refer to compound 5). Triethylamine (2.09 mL) was added to a solution of 2.00 g (10.0 mmol) of 1-(4-bromophenyl)ethylamine in 22.3 mL of dichloromethane and the mixture was cooled in an ice bath. Under argon protection and stirring, 2.87 mL (12.0 mmol) of di-tert-butyl dicarbonate was slowly added to the mixture. Subsequently, the reaction mixture was warmed to room temperature and stirring was continued for 1 hour. Upon completion of the reaction, the reaction solution was poured into 200 mL of water and extracted with 200 mL of chloroform. The organic layer was washed sequentially with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under vacuum. The resulting solid was washed twice with 10 mL of hexane to give 2.71 g of tert-butyl (1-(4-bromophenyl)ethyl)carbamate as a white powder (yield: 90%). rf value: 0.55 (n-hexane: ethyl acetate=4:1, v/v). Mass spectrum (FAB, m/z): 300, 302 (M++1). 1H-NMR spectrum (DMSO-d6, δ ppm): 1.27 (d, J=6.8 Hz, 3H), 1.36 (brs, 9H), 4.51-4.64 (m, 1H), 7.25 (d, J=8.3 Hz, 2H), 7.35-7.45 (m, 1H) , 7.49 (d, J=8.3 Hz, 2H).

References

[1] Patent: EP1679308, 2006, A1. Location in patent: Page/Page column 32-33
[2] Patent: WO2010/97410, 2010, A1. Location in patent: Page/Page column 125
[3] Patent: US2012/40942, 2012, A1. Location in patent: Page/Page column 58
[4] Angewandte Chemie - International Edition, 2008, vol. 47, # 7, p. 1287 - 1290
[5] Patent: WO2013/40790, 2013, A1. Location in patent: Page/Page column 40

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