4-Chlorotoluene → N,N-diethyl-p-toluidine

HRID 276152Notes

Reaction equation

HRID 276152 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[CH2:9]([NH:11][CH2:12][CH3:13])[CH3:10].CC([O-])(C)C.[K+].[Br-].[Li+]>C1(C)C=CC=CC=1>[CH2:9]([N:11]([C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1)[CH2:12][CH3:13])[CH3:10]

Participants

6

Reactant 4

HCID 78104-ChlorotolueneHCID 8021DiethylamineHCID 82050Lithium BromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 69177N,N-diethyl-p-toluidineYield 91%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20 mmol of p-chlorotoluene (2.53 g), 24 mmol of diethylamine (1.75 g), 28 mmol of KOtBu (3.13 g), 4 mmol of lithium bromide (0.35 g) and 44 mg of trans-di-μ-acetatobis[2-[bis(1,1-dimethylethyl)phosphino]-2-methylpropyl-C,P]dipalladium(II) (0.3 mol %) are suspended in 50 ml of toluene and refluxed for 24 hours. After cooling to room temperature, the salts are filtered off and washed with petroleum ether. The solvents are removed from the filtrate on a rotary evaporator. Distillation via a bulb tube (100° C./12 torr) gives 4-(N,N-diethylamino)toluene as a colorless liquid in a yield of 91%.

Workup

  1. temperaturerefluxed for 24 hours
  2. filtrationthe salts are filtered off
  3. washwashed with petroleum ether
  4. customThe solvents are removed from the filtrate on a rotary evaporator
  5. distillationDistillation via a bulb tube (100° C./12 torr)

Sources & evidence

ORD record
ord-2901c6889fab409c8ae6cea01ad2650b
Source dataset
uspto-grants-2002_03
Patent number
US06353136B1

Reaction notes

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