4,4'-Dimethoxydiphenylamine → 4-Methoxy-N,N-bis(4-methoxyphenyl)benzenamine

HRID 1871014

Reaction equation

HRID 1871014 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:14][CH:13]=1.C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([N:18]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:15]2[CH:16]=[CH:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 75714,4'-DimethoxydiphenylamineHCID 77304-BromoanisoleHCID 83681Tris(1,1-dimethylethyl)phosphine

Product 1

HCID 98625464-Methoxy-N,N-bis(4-methoxyphenyl)benzenamineYield 96%

Reagents, catalysts & solvents 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 1140TolueneSolvent

Procedure

The above general procedure was followed using 4-bromoanisole (187 mg, 1.00 mmol) and di(4-methoxyphenyl)amine (229 mg, 1.00 mmol) with 1 mol % Pd(dba)2 and 0.8 mol % tri-t-butylphosphine in 1.5 mL of toluene. After one hour, the reaction mixture was adsorbed onto silica gel and chromatographed with 5% ethyl acetate/hexanes to give 321 mg (96%) of tri(4-methoxyphenyl)amine as a white solid. 1H NMR (500 MHz, C6D6) δ 7.08 (d, J=10 Hz, 6 H), 6.73 (d, J=10 Hz, 6H), 3.31 (s, 9H). 13C NMR (125 MHz, C6D6) δ 155.7, 142.6, 125.3, 115.0, 55.0.

Workup

  1. customchromatographed with 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-8d0201c872a44139bea824b8d7168e6a
Source dataset
uspto-grants-2000_08
Patent number
US06100398

Linked notes

Loading…