2-Bromotoluene → Benzenamine, 2-methyl-N-(2-methylphenyl)-

HRID 1776070Notes

Reaction equation

HRID 1776070 reaction equation
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1.Br[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16].CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:3]1([CH3:8])[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16]

Participants

6

Reactant 3

HCID 72362-BromotolueneHCID 7242O-ToluidineHCID 23676156Sodium t-butoxide

Product 1

HCID 136423Benzenamine, 2-methyl-N-(2-methylphenyl)-Yield 89.7%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of o-toluidine (6.05 g, 56.5 mmol), 1-bromo-2-methylbenzene (8.5 g, 50 mmol), Pd(dppf)Cl2 and sodium tert-butoxide (9.6 g, 0.1 mmol) in toluene (120 mL) was degassed and heated at about 100° C. overnight. The mixture was purified by flash column using eluents of hexanes/dichloromethane 2:1 to give a white solid (Compound 9) (8.84 g, in 89.7% yield).

Workup

  1. customwas degassed
  2. customThe mixture was purified by flash column

Sources & evidence

ORD record
ord-d1c063c2601e4510a908a76ea9aaff91
Source dataset
uspto-grants-2016_02
Patent number
US09263681B2

Reaction notes

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