2-Bromotoluene → HCID 9794453, compound

HRID 1871022Notes

Reaction equation

HRID 1871022 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:8].[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.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:9]([N:13]([CH2:14][CH2:15][CH2:16][CH3:17])[C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 3

HCID 72362-BromotolueneHCID 8148DibutylamineHCID 83681Tris(1,1-dimethylethyl)phosphine

Product 1

HCID 9794453HCID 9794453, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

The above general procedure was followed using 2-bromotoluene (171 mg, 1.00 mmol) and dibutylamine (129 mg, 1.00 mmol) with 2 mol % Pd(OAc)2 and 1.6 mol % tri-t-butylphosphine in 1.0 mL of toluene. After 6 hours, the reaction mixture was adsorbed onto silica gel and chromatographed with 2% ethyl acetate/hexanes to give 181 mg (83%) of N,N-dibutyl-o-toluidine. 1H NMR (500 MHz, CDCl3) δ 7.18 (t, J=7.8 Hz, 1H), 7.13 (d, J=7.8 Hz, 1H), 7.08 (d, J=7.8 Hz, 1H), 6.97 (t, J=7.8 Hz, 1H), 2.91 (t, J=7.5 Hz, 4H), 2.30 (s, 3H), 1.41-1.37 (m, 4H), 1.27 (sept, J=7.3 Hz, 4H), 0.87 (t, J=7.3 Hz, 6H). 13C NMR (125 MHz, CDCl3) δ 150.7, 135.0, 130.9, 126.0, 123.1, 122.3, 53.9, 29.6, 20.5, 18.3, 14.0.

Workup

  1. customchromatographed with 2% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-84484ba28c8641d989d6cb54c26250a4
Source dataset
uspto-grants-2000_08
Patent number
US06100398

Reaction notes

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