Iodobenzene → 4-Amino-2'-methylbiphenyl

HRID 489871Notes

Reaction equation

HRID 489871 reaction equation
C1(C)C=CC([NH:7][C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)=CC=1.I[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O[Na])(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C(C)=CC=CC=1>[C:19]1([CH3:20])[CH:18]=[CH:17][CH:22]=[CH:21][C:14]=1[C:11]1[CH:10]=[CH:9][C:8]([NH2:7])=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 11575IodobenzeneHCID 11776TriphenylphosphineHCID 69293Benzenamine, 4-methyl-N-(4-methylphenyl)-HCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 1367994-Amino-2'-methylbiphenyl

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

10.0 g (50.7 mmols) of N,N-di(p-toluyl)amine (31b), 10.3 g (50.7 mmols) of 4-iodobenzene, 5.85 g (60.8 mmols) of t-BuONa, 300 mg (1.34 mmols) of Pd(CH3CO)2 and 1.50 g (5.71 mmols) of triphenylphosphine were dissolved in xylene and refluxed in an atmosphere of nitrogen for 4 hours.

Workup

  1. temperaturerefluxed in an atmosphere of nitrogen for 4 hours

Sources & evidence

ORD record
ord-7e8279a1378644438bc871a4a81240f4
Source dataset
uspto-grants-2005_12
Patent number
US06979746B2

Reaction notes

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