4-BROMO-2-METHOXY-BENZONITRILE Chemical Properties

Boiling point:

289.1±20.0 °C(Predicted)

Density 

1.56±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

crystalline solid

color 

Off-white

Safety Information

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

RIDADR 

3439

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

2926907090

4-BROMO-2-METHOXY-BENZONITRILE Usage And Synthesis

Uses

4-Bromo-2-methoxybenzonitrile is a useful intermediate for organic synthesis.

Synthesis

General procedure for the synthesis of 2-methoxy-4-bromobenzonitrile from methanol and 4-bromo-2-fluorobenzonitrile: 4-bromo-2-fluorobenzonitrile (15.0 g, 75.0 mmol), methanol (30.4 mL, 350 mmol), and potassium carbonate (31.1 g, 225 mmol) were dissolved in N,N-dimethylformamide (DMF, 150 mL) and the reaction was stirred overnight at 55°C under argon protection. The reaction was stirred at 55°C overnight under argon protection. Upon completion of the reaction, thin layer chromatography (TLC, spreading agent 100% dichloromethane) showed complete consumption of the material. The reaction mixture was poured into a mixture of ether (300 mL) and water (150 mL) and the organic layer was separated. The organic layer was washed sequentially with water (150 mL) and brine (50 mL), dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 2-methoxy-4-bromobenzonitrile (15.2 g, 95.5% yield) as a white solid. The structure of the product was confirmed by hydrogen nuclear magnetic resonance (1H-NMR, CDCl3) and gas chromatography (GC-MS): 1H-NMR (CDCl3) δ 7.41 (d, J = 8.1 Hz, 1H), 7.16 (dd, J = 8.1, 1.6 Hz, 1H), 7.13 (d, J = 1.6 Hz, 1H), 3.93 (s, 3H); GC- MS m/z = 211 (M+), retention time (RT) = 6.15 min.

References

[1] Patent: WO2005/14566, 2005, A1. Location in patent: Page/Page column 60
[2] Patent: WO2009/7747, 2009, A2. Location in patent: Page/Page column 43
[3] Patent: WO2010/116282, 2010, A1. Location in patent: Page/Page column 57
[4] Patent: WO2008/25509, 2008, A1. Location in patent: Page/Page column 91-92

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