Bromobenzene → HCID 59480060, compound

Participants

Reaction Steps

In a 300-mL three-neck flask were placed 200 mL of toluene, 0.21 g (0.96 mmol) of palladium acetate, and an ellipsoidal stirring chip. The two outer necks were closed with septum caps and the center neck was provided with a reflux coiled condenser. To the top of the condenser was attached a three-way stopcock, to which is attached a balloon filled with nitrogen gas. The atmosphere in the flask was replaced three times by nitrogen gas supplied from the balloon with the help of a vacuum pump. Into the flask was injected 3.8 g (18.9 mmol) of tris-t-butylphosphine by means of a syringe, followed by stirring for five to ten minutes at room temperature. The flask was further charged with 10 g (63.7 mmol) of 4-bromobenzene, 4.11 g (31.8 mmol) of 3,4-difluoroaniline, and 6.1 g (63.7 mmol) of sodium t-butoxide. With the flask placed on an oil bath, the solution therein was gradually heated to 120° C. with stirring. After 20 hours, the flask was dismounted from the oil bath so as to terminate reaction, and the solution was allowed to cool to room temperature in an atmosphere of nitrogen. The reaction solution was transferred to a separatory funnel and was given 70 mL of diethyl ether. It was washed several times with 100 mL of saturated aqueous solution of sodium chloride. The organic layer was separated and dried with anhydrous magnesium sulfate. With the anhydrous magnesium sulfate filtered out, the organic layer was freed of solvent by means of an evaporator. Thus there was obtained a crude product, which was subsequently purified by means of a silica gel column (hexane:chloroform=2:1) (Yields: 92%).

Provenance & Evidence