benzyl 2,4-difluorophenylcarbaMate

benzyl 2,4-difluorophenylcarbaMate Property

Boiling point:

312.1±42.0 °C(Predicted)

Density 

1.329±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

11.69±0.70(Predicted)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

benzyl 2,4-difluorophenylcarbaMate Chemical Properties,Usage,Production

Synthesis

To a 250 mL round bottom flask was added 2,4-difluoroaniline (11.4 g, 4.62 mL, 45.4 mmol), dichloromethane (DCM, 103 mL) and pyridine (7.40 mL, 91 mmol). The reaction mixture was stirred at room temperature and benzyl chloroformate (8.15 mL, 54.5 mmol) was slowly added dropwise through the addition funnel. After the dropwise addition, the reaction mixture was continued to be stirred at room temperature overnight. Upon completion of the reaction, the mixture was poured into water and extracted with DCM. The organic phases were combined, washed sequentially with water and saturated saline, and then dried over anhydrous sodium sulfate. After filtration to remove the desiccant, the filtrate was concentrated under reduced pressure to afford benzyl (2,4-difluorophenyl)-carbamate (11.1 g, 42.2 mmol, 93% yield) as a white solid, which could be used for subsequent reactions without further purification.LC-MS (ESI, positive ion mode) analysis: calculated value of C14H11F2NO2 [M+H]+: 263.1; Measured value: 263.1. measured value [M+Na]+: 286.1. 1H NMR (400 MHz, DMSO-d6) δ ppm: 9.43 (br s, 1H), 7.51-7.66 (m, 1H), 7.24-7.46 (m, 6H), 7.01-7.12 (m, 1H), 5.15 (s, 2H).

References

[1] Tetrahedron Letters, 2006, vol. 47, # 36, p. 6393 - 6396
[2] Canadian Journal of Chemistry, 2009, vol. 87, # 2, p. 393 - 396
[3] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 10, p. 2215 - 2234
[4] Tetrahedron Letters, 2008, vol. 49, # 16, p. 2607 - 2610
[5] Patent: US2008/167338, 2008, A1. Location in patent: Page/Page column 44-45