4-Methyl-3-(trifluoromethyl)benzoic acid → 4-(Bromomethyl)-3-(trifluoromethyl)benzoic acid

1.0 g of 4-methyl-3-(trifluoromethyl)benzoic acid was dissolved in isopropyl acetate (q.s.). To the mixture, sodium bromate aqueous solution (10 ml, containing 2.2 g of sodium bromate) and sodium bisulfite aqueous solution (10 ml, containing 1.52 g of sodium bisulfite) were added alternatively with stirring. After addition, the solution became brownish red. The mixture was heated to reflux until the solution became colorless. Then the organic layer was separated. Again, to the mixture, sodium bromate aqueous solution (10 ml, containing 2.2 g sodium bromate) and sodium bisulfite aqueous solution (10 ml, containing 1.52 g sodium bisulfite) were added alternatively and the mixture was heated to reflux until the solution became colorless. Then the organic layer was separated. Continually, to the mixture, a sodium bromate aqueous solution (10 ml, containing 2.2 g sodium bromate) and a sodium bisulfite aqueous solution (10 ml, containing 1.52 g sodium bisulfite) were added alternatively, and the mixture was heated to reflux until the solution became colorless. Then the organic layer was separated. The organic layer was washed with 5% sodium sulfate solution twice and 15% sodium chloride solution twice, dried over anhydrous Na2SO4, filtered, concentrated under reduced pressure to dry. The is residue was stirred in petroleum ether, and filtered to give a white solid. m.p. 140-145° C.

1. additionAfter addition
2. temperatureThe mixture was heated
3. temperatureto reflux until the solution
4. customThen the organic layer was separated
5. additionAgain, to the mixture, sodium bromate aqueous solution (10 ml, containing 2.2 g sodium bromate) and sodium bisulfite aqueous solution (10 ml, containing 1.52 g sodium bisulfite) were added alternatively
6. temperaturethe mixture was heated
7. temperatureto reflux until the solution
8. customThen the organic layer was separated
9. additionContinually, to the mixture, a sodium bromate aqueous solution (10 ml, containing 2.2 g sodium bromate) and a sodium bisulfite aqueous solution (10 ml, containing 1.52 g sodium bisulfite) were added alternatively
10. temperaturethe mixture was heated
11. temperatureto reflux until the solution
12. customThen the organic layer was separated
13. washThe organic layer was washed with 5% sodium sulfate solution twice
14. dry with material15% sodium chloride solution twice, dried over anhydrous Na2SO4
15. filtrationfiltered
16. concentrationconcentrated under reduced pressure
17. customto dry
18. stirringThe is residue was stirred in petroleum ether
19. filtrationfiltered
20. customto give a white solid

ORD record

ord-9c45df9794e847b1bb1519d14107bcf8

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426446B2