Main applications of o-fluoroanisole_Kain Industrial Additives

Background and overview^[1]

O-Fluoroanisole can be used as a pharmaceutical synthesis intermediate. If o-fluoroanisole is inhaled, please move the patient to fresh air; if the skin comes into contact, take off contaminated clothing, rinse the skin thoroughly with soap and water, and seek medical treatment if you feel uncomfortable; if the eye contact occurs, seek medical attention. Separate eyelids, rinse with running water or saline, and seek medical attention immediately; if ingested, rinse mouth immediately, do not induce vomiting, and seek medical attention immediately.

Preparation^[1]

The preparation of o-fluoroanisole is as follows:

The specific steps are as follows: Dissolve o-fluorophenol (4.0g, 35.7mmol) in tetrahydrofuran (30mL), add potassium carbonate (18.5g, 0.13mol) and dimethyl sulfate (4.2mL, 44.3mmol), obviously The reaction was exothermic at 50°C for 1 hour, and TLC showed that the raw materials had disappeared. Filter off potassium carbonate, wash the solid with ethyl acetate (3×20mL), combine the organic phases, dry over anhydrous magnesium sulfate, and concentrate under reduced pressure (water pump) to obtain light yellow oily liquid o-fluoroanisole (3.74g, yield 83%). δ_H(300MHz; CDCl₃)7.07-6.84(4H, m), 3.87(3H, s).

Application

O-Fluoroanisole can be used as a pharmaceutical synthesis intermediate. If the following reaction occurs:

The specific steps are as follows: Dissolve the crude product of o-fluoroanisole (1.0g, 7.9mmol) in acetonitrile (15mL), add N-bromosuccinimide (1.4g, 8.7mmol), and stir at 70 React for 3 hours at ℃. TLC shows that the raw materials have been reacted. Most of the acetonitrile is evaporated, 30 mL of water is added, stirred for 10 min, extracted with ethyl acetate (3×20 mL), the organic phases are combined, dried over anhydrous magnesium sulfate and subjected to column chromatography. After separation (pure petroleum ether was used as eluent), the brominated product was obtained as a light yellow oily liquid (1.4 g, yield 86%). A-2c: δ_H (300MHz; CDCl₃) 7.23-7.16 (2H, m), 6.82 (1H, t, J=8.7Hz), 3.86 (3H , s); δ_C (75MHz; CDCl₃)152.3 (d, J_C_,_F=249.0Hz), 147.1 (d, J=10.4Hz), 127.2 (d, J=4.0Hz), 119.6 (d, J=21.1Hz), 114.6 (d, J=2.2Hz), 111.9 (d, J=8.2Hz), 56.4.