Simple methods of preparing substituted deuteriobenzenes and α-deuteriotoluenes of high isotopic purity

Abstract

Deuteriobenzenes, XC₆H₄D (X = H, o-, m-, or p-Me, m- or p-Cl, m- or p-OMe, m-CF₃, p-F, or p-Br), of better than 98% isotopic purity have been prepared by treatment of the appropriate aryltrimethylstannane, XC₆H₄·SnMe₃, with O-deuterioacetic acid containing 10%(w/w) of deuterium oxide at 75°. The benzyl compound m-CF₃·C₆H₄·-CH₂D has been correspondingly prepared by treatment of the compound m-CF₃·C₆H₄·CH₂·SiMe₃ with sodium deuterioxide in O-deuteriomethanol. The methods should have general application.