Phenyl-1-naphthylamine → N-(4'-bromo-[1,1'-biphenyl]-4-yl)-N-phenylnaphthalen-1-amine

HRID 1928667

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:15]1([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:25]([C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 4,4′-dibromobiphenyl (8.46 g=27.4 mmol), Pd(OAc)2 (105 mg=0.18 mmol), dppf (253 mg=0.46 mmol), N-(1-naphthyl)aniline (2.0 g=9.13 mmol) and sodium t-butoxide (1.32 g=13.7 mmol) in dry toluene was placed in a three-necked flask under a nitrogen atmosphere and stirred at 90° C. for 15 h. After cooling, the reaction was quenched by adding water and then extracted by ethyl acetate. The organic layer was dried over anhydrous MgSO4 and evaporated under vacuum. The products were purified by a silica gel column eluted with hexane. White solid of compound 2N was obtained in 70% yield (2.86 g=6.37 mmol).

Workup

customwas placed in a three-necked flask under a nitrogen atmosphere
temperatureAfter cooling
customthe reaction was quenched
additionby adding water
extractionextracted by ethyl acetate
dry with materialThe organic layer was dried over anhydrous MgSO4
customevaporated under vacuum
customThe products were purified by a silica gel column
washeluted with hexane

Sources & evidence

ORD record: ord-445ad050c76a4e5ca7eae9f41f26deb5
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183393B2

Linked notes

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