4-Bromo-3-fluoroanisole Chemical Properties

Melting point:

217-219°C

Boiling point:

195.4±20.0 °C(Predicted)

Density 

1.60

refractive index 

1.5410-1.5450

Flash point:

85°(185°F)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

clear liquid

color 

Colorless to Light yellow to Light orange

InChI

InChI=1S/C7H6BrFO/c1-10-5-2-3-6(8)7(9)4-5/h2-4H,1H3

InChIKey

XANVIFOBBVAKCY-UHFFFAOYSA-N

SMILES

C1(Br)=CC=C(OC)C=C1F

CAS DataBase Reference

458-50-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

23-26-37-60

RIDADR 

1993

HazardClass 

IRRITANT

PackingGroup 

Ⅲ

HS Code 

29093090

4-Bromo-3-fluoroanisole Usage And Synthesis

Chemical Properties

Clear colorless to light yellow liquid

Uses

4-Bromo-3-fluoroanisole is a halo-aryl compound used in the preparation of orally available mGlu1 receptor enhancers.

Synthesis

Step 1: Synthesis of 1-bromo-2-fluoro-4-methoxybenzene To a 250 mL round bottom flask was added 4-bromo-3-fluorophenol (5.0 g, 26.18 mmol, 1.00 equiv) and tetrahydrofuran (50 mL). Subsequently, potassium hydroxide (2.94 g, 52.40 mmol, 2.00 equiv) was added in batches. Under stirring, iodomethane (5.6 g, 39.45 mmol, 1.51 eq.) was added dropwise. The reaction mixture was stirred at 30°C for 4 h. The progress of the reaction was monitored by thin layer chromatography (TLC, unfolding agent ratio petroleum ether:ethyl acetate = 1:4). Upon completion of the reaction, the reaction was quenched by the addition of 30 mL of water. The reaction mixture was extracted with ethyl acetate (3 x 30 mL), the organic layers were combined and dried with anhydrous sodium sulfate. Subsequently, the organic layer was concentrated under reduced pressure to obtain the crude product. The crude product was purified by silica gel column chromatography using petroleum ether as eluent to give 5.2 g (97% yield) of 1-bromo-2-fluoro-4-methoxybenzene as a yellow oil.

References

[1] Patent: US2014/275179, 2014, A1. Location in patent: Paragraph 0738; 0739
[2] Patent: US9067898, 2015, B1. Location in patent: Page/Page column 57; 58
[3] Patent: WO2015/134039, 2015, A1. Location in patent: Page/Page column 69-70
[4] Angewandte Chemie - International Edition, 2016, vol. 55, # 12, p. 3909 - 3913
[5] Angew. Chem., 2016, p. 3977 - 3981,5

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