2-BROMO-5-CHLOROBENZYL ALCOHOL Chemical Properties

Melting point:

81-83°C

Boiling point:

290℃

Density 

1.685

Flash point:

129℃

storage temp. 

Sealed in dry,Room Temperature

pka

13.67±0.10(Predicted)

form 

solid

2-BROMO-5-CHLOROBENZYL ALCOHOL Usage And Synthesis

Uses

2-Bromo-5-chlorobenzyl Alcohol is used to prepare fluorodihydrohydroxy benzoxaborole for potential treatment of onychomycosis. It is also an intermediate used to synthesize morpholylureas as potent and selective inhibitors of AKR1C3.

Synthesis

Under nitrogen protection, 2-bromo-5-chlorobenzoic acid (17-1, 5.0 g, 21.23 mmol) was dissolved in BH3/THF solution (1 M, 85 mL) at a controlled temperature of 10 °C. After the addition was completed, the reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, methanol (30 mL) was added slowly at 0 °C to quench the reaction, after which the mixture was concentrated to dryness. The resulting residue was dissolved in methanol (100 mL) and concentrated again to dryness. This dissolution-concentration procedure was repeated twice to give 2-bromo-5-chlorobenzenemethanol (17-2) as a white solid (4.7 g, quantitative yield).

References

[1] Patent: US9138427, 2015, B2. Location in patent: Page/Page column 295
[2] Patent: WO2012/131588, 2012, A1. Location in patent: Page/Page column 96; 108
[3] Chemical Communications, 2018, vol. 54, # 20, p. 2467 - 2470
[4] Journal of Medicinal Chemistry, 2006, vol. 49, # 15, p. 4447 - 4450
[5] Patent: US2007/265226, 2007, A1. Location in patent: Page/Page column 58

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