Haloform Reaction

This reaction has been used in qualitative analysis to indicate the presence of a methyl ketone. The product iodoform is yellow and has a characteristic odour. The reaction has some synthetic utility in the oxidative demethylation of methyl ketones if the other substituent on the carbonyl groups bears no enolizable α-protons.

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Mechanism of the Haloform Reaction

The reaction readily proceeds to completion because of the acidifying effect of the halogen substituents.

Recent Literature

Novel and Direct Transformation of Methyl Ketones or Carbinols to Primary Amides by Employing Aqueous Ammonia
L. Cao, J. Ding, M. Gao, Z. Wang, J. Li, A. Wu, Org. Lett., 2009, 11, 3810-3813.

Iodine-Mediated Domino Protocol for the Synthesis of Benzamides from Ethylarenes via sp³ C-H Functionalization
K. S. Vadagaonkar, H. P. Kalmode, S. Prakash, A. C. Chaskar, Synlett, 2015, 26, 1677-1682.

Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I₂-Aqueous NH₃
S. Shimokawa, Y. Kawagoe, K. Moriyama, H. Togo, Org. Lett., 2016, 18, 784-787.