1,10-Phenanthroline → 4-Bromotriphenylamine

Reaction equation

[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.I[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH-].[K+].N1[C:31]2[C:22](=[CH:23][CH:24]=[C:25]3[C:30]=2N=CC=C3)C=CC=1>>[C:10]1([N:6]([C:5]2[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][CH:4]=2)[C:22]2[CH:31]=[CH:30][CH:25]=[CH:24][CH:23]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Reactant 4

HCID 13181,10-Phenanthroline

HCID 78074-Bromoaniline

HCID 11575Iodobenzene

HCID 14797Potassium Hydroxide

Product 1

HCID 6428384-BromotriphenylamineYield 161.9%

Conditions

Temperature: 180 °C

Procedure

To a 500 ml flask, 17.2 g (0.1 mol) of 4-bromoaniline, 50 g (0.24 mol) of iodobenzene, 32 g (0.8 mol) of potassium hydroxide, 0.04 g (0.04 mol, 0.4 eq.) of cuprous chloride and 0.08 g (0.04 mol, 0.4 eq.) of phenanthroline were introduced and stirred for 12 hours at 180° C. under nitrogen atmosphere. The reaction mixture was cooled to room temperature and the insoluble solid salt was filtered off. The filtrate was extracted with toluene and distilled water two times and then the organic layer was collected. Toluene was removed from the organic layer under reduced pressure to provide an organic compound. The organic compound was purified by column chromatography using n-hexane as an eluent. Then, the product was precipitated with a small amount of ethanol to provide 21 g of diphenylamino 4-bromobenzene (yield 65%). m/z 324 (M+).