3-FLUORO-4-METHOXYBENZYL BROMIDE Chemical Properties

Melting point:

44-46°C

Boiling point:

149-155 °C(Press: 25-28 Torr)

Density 

1.488±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

color 

Red

Sensitive 

Lachrymatory

CAS DataBase Reference

331-61-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

C,Xn

Risk Statements 

36/37/38-52-22-34

Safety Statements 

26-36/37/39-45

RIDADR 

UN3261

Hazard Note 

Corrosive/Lachrymatory

HazardClass 

8

PackingGroup 

III

HS Code 

29093090

3-FLUORO-4-METHOXYBENZYL BROMIDE Usage And Synthesis

Chemical Properties

White solid

Synthesis

The general procedure for the synthesis of 3-fluoro-4-methoxybenzyl bromide from (3-fluoro-4-methoxyphenyl)methanol was as follows: at room temperature, (3-fluoro-4-methoxyphenyl)methanol (2.35 g, 15.05 mmol) and triethylamine (3.15 mL, 22.58 mmol) were dissolved in anhydrous dichloromethane (50 mL). Subsequently, methanesulfonyl chloride (1.41 mL, 18.06 mmol) was added dropwise. After 15 minutes of reaction, the reaction mixture was diluted with dichloromethane (50 mL) and the organic layer was washed with saturated aqueous sodium bicarbonate solution. The organic layer was separated, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was dissolved in anhydrous acetone (100 mL), excess lithium bromide was added and the mixture was heated to reflux for 30 minutes. After the reaction was complete, the solution was cooled and the solvent was evaporated under reduced pressure. The residue was partitioned between ethyl acetate and water and the aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the target product 3-fluoro-4-methoxybenzyl bromide (3.00 g, 91% yield). The structure of the product was confirmed by 1H NMR (CDCl3): δ7.16-7.07 (2H, m), 6.90 (1H, dd, J=8.3,8.4Hz), 4.45 (2H, s), 3.89 (3H, s).

References

[1] Patent: WO2017/155909, 2017, A1. Location in patent: Paragraph 0120
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 24, p. 6842 - 6846
[3] Chemical Biology and Drug Design, 2016, p. 97 - 109

3-FLUORO-4-METHOXYBENZYL BROMIDE(331-61-3)Related Product Information

• 3-FLUORO-4-(TRIFLUOROMETHOXY)BENZYL BROMIDE
• 3-FLUORO-4-METHOXYBENZYL BROMIDE
• 4-METHOXYTETRAFLUOROBENZYL BROMIDE
• 3-CHLORO-5-FLUORO-4-METHOXYBENZYL BROMIDE
• 3,5-DIFLUORO-4-METHOXYBENZYL BROMIDE
• 2,3-DIFLUORO-4-METHOXYBENZYL BROMIDE
• 2-CHLORO-6-FLUORO-3-METHOXYBENZYL BROMIDE
• 2-FLUORO-6-METHOXYBENZYL BROMIDE
• 5-Fluoro-2-methoxybenzyl bromide, 98+%,5-FLUORO-2-METHOXYBENZYL BROMIDE 97,5-Fluoro-2-methoxybenzyl bromide 97%,5-FLUORO-2-METHOXYBENZYL BROMIDE
• 6-CHLORO-2-FLUORO-3-METHOXYBENZYL BROMIDE
• 4-FLUORO-2-METHOXYBENZYL BROMIDE
• 4-FLUORO-3-METHOXYBENZYL BROMIDE
• 2,6-DIFLUORO-4-METHOXYBENZYL BROMIDE
• 4-Methoxybenzyl bromide
• 3-FLUORO-5-METHOXYBENZYL BROMIDE
• 3-FLUORO-2-METHOXYBENZYL BROMIDE
• 2-FLUORO-4-METHOXYBENZYL BROMIDE