Iodobenzene → 2-Methyl-N-(2-methylphenyl)-N-phenylaniline

HRID 1776071Notes

Reaction equation

HRID 1776071 reaction equation
[C:1]1([CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14].I[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.P(C(C)(C)C)(C(C)(C)C)C(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:15][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14]

Participants

7

Reactant 4

HCID 11575IodobenzeneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 136423Benzenamine, 2-methyl-N-(2-methylphenyl)-2×HCID 23676156Sodium t-butoxide

Product 1

HCID 227213082-Methyl-N-(2-methylphenyl)-N-phenylanilineYield 98%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of di-o-tolylamine (Compound 9) (6.00 g, 30.4 mmol), iodobenzene (12.2 g, 60 mmol), Pd(OAc)2 (0.34 g, 1.5 mmol), P(t-Bu)3 (0.6 g, 3 mmol), sodium tert-butoxide (5.76 g, 60 mmol) in toluene (120 mL) was degassed and heated at about 120° C. for 40 hours. The resulting mixture was diluted with ethyl acetate (200 mL), washed with brine, dried over Na2SO4, loaded on silica gel and purified by flash column using eluents of hexanes to give a white solid (Compound 10) (8.2 g, in 98% yield).

Workup

  1. customwas degassed
  2. additionThe resulting mixture was diluted with ethyl acetate (200 mL)
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. custompurified by flash column

Sources & evidence

ORD record
ord-6f78a0f7ecf947668096df29db98319e
Source dataset
uspto-grants-2016_02
Patent number
US09263681B2

Reaction notes

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