Acetic Acid → 6-Bromo-2-(3-phenoxybenzoyl)-pyridine

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]=2)[OH:9])[CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>O.[O-2].[O-2].[O-2].[Cr+6]>[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:9])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:11]=2)[CH:5]=[CH:4][CH:3]=1

Participants

Procedure

A solution of 5 g chromium trioxide in 10 ml water is added to a mixture of 20 g 6-bromo-α-(3-phenoxyphenyl)-2-pyridinemethanol (see Ex. 18) and 70 ml glacial acetic acid. After stirring for 1 hr. at room temperature, the reaction mixture is added to ice:water and extracted with chloroform. The organic layer is washed with 2.5N NaOH, then with water, dried (Na2SO4) and solvent removed. Yield: 15.4 g of the title product, m.p. 65°-6° C. (from methanol); Br 22.87 (22.56).