4-BROMOMETHYL-3-FLUOROBENZOIC ACID METHYL ESTER

4-BROMOMETHYL-3-FLUOROBENZOIC ACID METHYL ESTER Property

Melting point:

68 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))

Boiling point:

295.1±35.0 °C(Predicted)

Density 

1.534±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

color 

White

Safety

HS Code 

2916399090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

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

P280Wear protective gloves/protective clothing/eye protection/face protection.

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

4-BROMOMETHYL-3-FLUOROBENZOIC ACID METHYL ESTER Chemical Properties,Usage,Production

Uses

Methyl 4-(bromomethyl)-3-fluorobenzoate

Synthesis

Bromination reaction: Methyl 3-fluoro-4-methylbenzoate (18.3 mmol) was dissolved with N-bromosuccinimide (NBS, 3.9 g, 22 mmol) in carbon tetrachloride (40 mL), and benzoyl peroxide (0.55 g, 1.7 mmol) containing 25% water was added as initiator. The reaction mixture was stirred well and heated to reflux for 6 hours. Upon completion of the reaction, the solvent was removed by evaporation and the residue was treated with an aqueous solution of potassium carbonate (K2CO3) followed by extraction of the product with ethyl acetate (EtOAc). After treatment, methyl 3-fluoro-4-(bromomethyl)benzoate was obtained as a light yellow solid in a yield of 5.9 g. The product was analyzed by electrospray ionization mass spectrometry (ESI-MS), which showed the [M + H]+ peak as 247 Da.

References

[1] Patent: WO2014/102376, 2014, A1. Location in patent: Page/Page column 45
[2] Patent: WO2014/102377, 2014, A1. Location in patent: Page/Page column 49-50
[3] Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6058 - 6080
[4] Synlett, 2014, vol. 25, # 17, p. 2485 - 2487
[5] Patent: US2006/14945, 2006, A1. Location in patent: Page/Page column 60