4,4'-Dimethoxydiphenylamine → 4-Methyltriphenylamine

HRID 1061092Notes

Reaction equation

HRID 1061092 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13](OC)=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.I[C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=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:22]1([CH3:25])[CH:23]=[CH:24][C:19]([N:9]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:6]2[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=2)=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 75714,4'-DimethoxydiphenylamineHCID 11776TriphenylphosphineHCID 122074-IodotolueneHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 112999284-Methyltriphenylamine

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

9.70 g (57.3 mmols) of N,N-diphenylamine (31a), 12.5 g (57.3 mmols) of 4-iodotoluene (32b), 6.61 g (68.8, mmols) of t-BuONa, 260 mg (1.15 mmols) of Pd(CH3COO)2 and 1.20 g (4.58 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-3496ca2e3882483fbbf25aa955b7ca59
Source dataset
uspto-grants-2003_02
Patent number
US06525212B1

Reaction notes

Loading…