反应详情

5.50 g (20 mmol) of 2-(2-chlorobenzyloxy)-5-fluorobenzoic acid are dissolved in 25 ml of THF, heated to reflux and then 20 ml of 1 M borane-dimethyl sulfide complex are added dropwise. The mixture is then cooled to room temperature and stirred at this temperature for 1 h. The solvent is distilled out in vacuo, and water is added to the residue. Acidification is then carried out cautiously (copious gas evolution) with 1 N hydrochloric acid. 1 N sodium hydroxide solution is then added to make slightly basic, and the aqueous phase is extracted three times with dichloromethane. The organic phases are dried over magnesium sulfate, filtered and washed with dichloromethane, and concentrated. Petroleum ether is added to the residue, and the crystals which have separated out are filtered off with suction and dried on a clay dish. 3.65 g (13.6 mmol, 68% of theory) of the title compound are obtained.

1. temperatureheated
2. temperatureto reflux
3. addition20 ml of 1 M borane-dimethyl sulfide complex are added dropwise
4. distillationThe solvent is distilled out in vacuo, and water
5. additionis added to the residue
6. addition1 N sodium hydroxide solution is then added
7. extractionthe aqueous phase is extracted three times with dichloromethane
8. dry with materialThe organic phases are dried over magnesium sulfate
9. filtrationfiltered
10. washwashed with dichloromethane
11. concentrationconcentrated
12. additionPetroleum ether is added to the residue
13. customthe crystals which have separated out
14. filtrationare filtered off with suction
15. customdried on a clay dish