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Categories: C-C Bond Formation > Heteroatom-containing Molecules > Trihalomethyl Carbinols

Synthesis of tribromomethyl carbinols

Recent Literature

Trihaloacetic acids can been converted to trichloromethyl and tribromomethyl ketones in good yield by a catalyzed reaction with aldehydes followed by oxidation. A coupling of organozinc intermediates with trichloroacetyl chloride gives trichloromethyl ketones.
E. J. Corey, J. O. Link, Y. Shao, Tetrahedron Lett., 1992, 33, 3435-3438.

TiCl4-Mg mediates the addition of CHBr3 or CBr3 depending on the reaction conditions to various aldehydes and ketones to form dibromomethyl carbinols and tribromomethyl carbinols respectively. The successful application of TiCl4-Mg-promoted coupling of CHBr3 with highly enolizable ketones such as 2-indanone and β-tetralone highlights the extraordinary reactivity and selectivity and the weakly basic nature of this system.
T.-H. Yan, S.-H. Chang, C.-T. Chang, C.-K. Lin, C.-Y. Liu, Org. Lett., 2013, 15, 5802-5805.