2-Methoxyaniline → 2-methoxyphenylaniline

HRID 403140Notes

Reaction equation

HRID 403140 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].Br[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.CC(C)([O-])C.[Na+]>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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CCOC(C)=O.C1(C)C(C)=CC=CC=1>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH:5][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

8

Reactant 4

HCID 70002-MethoxyanilineHCID 7961BromobenzeneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxide

Product 1

HCID 109105142-methoxyphenylaniline

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 1 L three neck flask was charged with 2-methoxyaniline (17.65 g, 143 mmol) , bromobenzene (15 g, 96 mmol), Pd2(dba)3 (1.75 g, 1.91 mmole), S-Phos (1.56 g, 3.82 mmol), sodium tert-butoxide (18.36 g, 101 mmol) and 400 mL of xylene. The reaction mixture was refluxed for 4 hours. The product was isolated by column chromatography (5% EtOAc in hexanes) to yield the desired product. (18 g, 94%)

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours

Sources & evidence

ORD record
ord-935d78f8a3594b03a6db292ffe1e8519
Source dataset
uspto-grants-2014_06
Patent number
US08748011B2

Reaction notes

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