Methyl 2-bromo-4-fluorobenzoate Chemical Properties

Boiling point:

75-78/1mm

Density 

1.577

Flash point:

100℃

storage temp. 

Sealed in dry,Room Temperature

Appearance

Colorless to light yellow Liquid

InChI

InChI=1S/C8H6BrFO2/c1-12-8(11)6-3-2-5(10)4-7(6)9/h2-4H,1H3

InChIKey

JENBPOJAZCPSEW-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=C(F)C=C1Br

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2916399090

Methyl 2-bromo-4-fluorobenzoate Usage And Synthesis

Uses

Methyl 2-bromo-4-fluorobenzoate is a carboxylic acid ester derivative used as an organic intermediate.

Chemical Properties

off-white powder

Synthesis

DBU (1.7 equiv, 1.16 mL, 7.76 mmol) was added to a solution of 2-bromo-4-fluorobenzoicacid (1.0equiv, 1.0 g, 4.57 mmol) and iodomethane (2.0 equiv, 0.57 mL, 9.14 mmol) in CH3CN(11 mL) at 23 °C. After stirring for 48 h, the reaction was quenched with H2O(10 mL) and extracted with Et2O (2 x 10 mL). The combined organic extracts were washed with water (20 mL) and brine (20 mL), dried over Na2SO4 and filtrated. Evaporation of the solvent under reduced pressure followed by flash chromatography (SiO2, 95/5 hexane/EtOAc) afforded 1.0 g (98%)of Methyl 2-bromo-4-fluorobenzoate as a colourless oil.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 20, p. 4393 - 4398
[2] Patent: US6407250, 2002, B1
[3] Patent: US6511999, 2003, B2
[4] Patent: US2002/128233, 2002, A1
[5] Patent: US2004/162323, 2004, A1

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