1-Bromo-4-tert-butylbenzene → HCID 20590576, compound

HRID 1361584Notes

Reaction equation

HRID 1361584 reaction equation
CC([O-])(C)C.[Na+].Br[C:8]1[CH:13]=[CH:12][C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:10][CH:9]=1.[CH3:18][N:19]([CH3:25])[CH2:20][CH2:21][CH2:22][NH:23][CH3:24]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[C:14]([C:11]1[CH:12]=[CH:13][C:8]([N:23]([CH3:24])[CH2:22][CH2:21][CH2:20][N:19]([CH3:25])[CH3:18])=[CH:9][CH:10]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 775951-Bromo-4-tert-butylbenzeneHCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 23676156Sodium t-butoxide

Product 1

HCID 20590576HCID 20590576, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a sealed tube was added Pd(OAc)2 (105 mg 0.469 mmol), NaOtBu (1.35 g, 14.07 mmol), 1-Bromo-4-tert-butylbenzene (2.0 g, 9.38 mmol), N,N, N′-Trimethyl-propane-1,3-diamine (1.65 mL, 11.26 mmol), P(iBuNCH2CH2)3N (133 μL, 0.375 mmol), and 5 mL toluene. The solution was heated to 80° C. for 1 h, cooled to RT, filtered through a pad of silica gel (rinsing with 10% MeOH/CH2Cl2), and concentrated in vacuo to yield the title compound (2.0 g, 86%) as a dark brown oil. MS (M+H)+=249; Calc'd 248.41 for C16H28N2.

Workup

  1. temperaturecooled to RT
  2. filtrationfiltered through a pad of silica gel (rinsing with 10% MeOH/CH2Cl2)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-386c7e4576d44247b3c83f60197441fd
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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