N-Methylaniline → 4-methoxy-N-methyl-N-phenylaniline

HRID 1871018Notes

Reaction equation

HRID 1871018 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH3:10][NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[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:11]([CH3:10])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 7515N-MethylanilineHCID 77304-BromoanisoleHCID 83681Tris(1,1-dimethylethyl)phosphine

Product 1

HCID 37351784-methoxy-N-methyl-N-phenylanilineYield 102.2%

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 N-methylaniline (107 mg, 1.00 mmol) with 1 mol % Pd(dba)2 and 0.8 mol % tri-t-butylphosphine in 1.0 mL of toluene. After 6 hours, the reaction mixture was adsorbed onto silica gel and chromatographed with 5% ethyl acetate/hexanes to give 218 mg (>99%) of N-(4-methoxyphenyl)-N-methylaniline. 1H NMR (500 MHz, CDCl3) δ 7.21 (dd, J=8.9, 7.0 Hz, 2H), 7.12 (d, J=8.8 Hz, 2H), 6.91 (d, J=8.8 Hz, 2H), 6.81 (d, J=8.4 Hz, 2H), 6.80 (t, J=7.0 Hz, 1H), 3.83 (s, 3H), 3.28 (s, 3H). 13C NMR (125 MHz, CDCl3) δ 156.3, 149.8, 142.4, 128.9, 126.1, 118.5, 115.9, 114.8, 55.5, 40.4.

Workup

  1. customchromatographed with 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6598d7cbc952431c954c1e24ad627412
Source dataset
uspto-grants-2000_08
Patent number
US06100398

Reaction notes

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