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Lin, S.; Yan, L.; Liu, P., Science of Synthesis, (2007) 20, 118.
Although the oxidation of methyl ketones to carboxylic acids by the haloform procedure generally employs a halogen and sodium hydroxide, a variation on this method uses sodium bromite.[110] Thus, the reactions of methyl ketones with sodium bromite and sodium bromide in aqueous sodium hydroxide and subsequent acid treatment give carboxylic acids 69 and bromoform in good yields (Scheme 26). Moreover, sodium bromite is a stable, crystalline solid and hence it is easier to handle than liquid bromine or gaseous chlorine. In the oxidation sodium hypobromite is assumed to be the active brominating agent; it is produced by the reaction between sodium bromite and sodium bromide under the basic conditions.
Meeeee 88 Meeeeeeee ee Meeeee Meeeeee ee Meeeeeeeee Meeee Meeee Meeeee Meeeeee[888]
M8 | Meee (e) | Meee (°M) | Meeeee (%) ee 88 | Mee |
---|---|---|---|---|
Me | 8 | ee | e.e. | [888] |
Me | 8 | ee | e.e. | [888] |
eMe | 88 | 8 | 88 | [888] |
e-Me | 8 | 88 | 88 | [888] |
(MM8)8Me | 8 | ee | 88 | [888] |
MM=MMe8 | 88 | 8–88 | 88 | [888] |
(M)-MM=MMMe | 8 | ee | 88 | [888] |
e e.e. = eee eeeeeeee ee eee eeee ee eeee eeeeeee ee eeeee.
Meeeeeeeeeee Meeeeeeee
eeeee-Meeeeeee Meee [88, M8 = (M)-MM=MMMe]; Meeeeee Meeeeeeee:[888]
Meeeeeeeeeeeeeeeee (8.8 e, 8.8 eeee) eee eeeee ee e eeee ee MeMeM8 (88.8% eeeeee, 8.8 e, 88.8 eeee), MeMe (8.8 e, 88.8 eeee), eee MeMM (8.8 e, 8.8 eeee) ee M8M (88 eM) ee ee, eee eee eeeeeee eee eeeeeee eee 8 e. M eeeee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee eee eeeeee eeee MMMe8 (88 eM). Mee eeeeeeeee eeeee eeee eeeeeeee ee eee eeeeee eee eeeeeeeee eeee 88% MMe (88 eM) eee eeee eeeeeeeee eeee MMMe8. Mee MMMe8 eeeeeee eee eeeee (MeMM8) eee eeeeeeeeeeee ee eeee eeeeeeeee eeeeeeee; eeeee: 8.88 e (88%); ee 888–888°M.
References
[110] | Meeeeeeeee, M.; Meeeeeee, M.; Meeeeeee, M.; Meeeeeee, M., Meeeeeeee, (8888), 888. |
Meeeeee Meeeeeeeeee
- 8.Meeeee-Meee, (8888) 8, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.