4-Chlorotoluene → HCID 10130667, compound

HRID 1871021Notes

Reaction equation

HRID 1871021 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[CH2:9]([NH:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:10][CH2:11][CH3:12].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]>[CH2:9]([N:13]([CH2:14][CH2:15][CH2:16][CH3:17])[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1)[CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 78104-ChlorotolueneHCID 8148DibutylamineHCID 83681Tris(1,1-dimethylethyl)phosphine

Product 1

HCID 10130667HCID 10130667, compoundYield 90%

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-chlorotoluene (126 mg, 1.00 mmol) and dibutylamine (129 mg, 1.00 mmol) with 1 mol % Pd(dba)2 and 0.8 mol % tri-t-butylphosphine in 1.0 mL of toluene. After 4 hours at 70° C., the reaction mixture was adsorbed onto silica gel and chromatographed with 2% ethyl acetate/hexanes to give 196 mg (90%) of N,N-dibutyl-p-toluidine.

Workup

  1. customchromatographed with 2% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-15ba19e107ce4030a86c0434522e3092
Source dataset
uspto-grants-2000_08
Patent number
US06100398

Reaction notes

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