Aniline → HCID 13087228, compound

HRID 749635Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:11][CH:10]=1>>[C:2]1([NH:1][C:20]2[C:15]([C:12]3[CH:11]=[CH:10][CH:9]=[CH:14][CH:13]=3)=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 6115Aniline2×

HCID 71014-Bromobiphenyl

Product 1

HCID 13087228HCID 13087228, compound

Procedure

An improved process for producing diarylamines is to react an arylbromide and an aniline compound in the presence of a suitable catalyst. For example, aniline can be rapidly reacted with 4-bromobiphenyl to form N-phenyl-biphenylamine using palladium acetate ligated with 2,4,6-trioxa-1,3,5,7-tetramethyl-8-phosphaadamantane, which is manufactured as Cytop-216 (Cytec Industries), and sodium t-pentoxide base. This reaction proceeds rapidly, in about 4 to 6 hours, to produce the desired diarylamine.

Sources & evidence

ORD record: ord-4daf5aef6bb64df0a5597f5a951f065c
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402700B2

Reaction notes

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