Acetonitrile → HCID 66891782, compound

HRID 250179Notes

Reaction equation

HRID 250179 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([CH3:20])[CH:14]=2)([CH2:11][CH3:12])[CH2:9][CH3:10])=[CH:4][CH:3]=1.CC#N.C([O-])([O-])=O.[K+].[K+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CCOCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[C:15]([CH3:20])[CH:14]=2)([CH2:11][CH3:12])[CH2:9][CH3:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 574435224-[1-(4-Bromophenyl)-1-ethylpropyl]-2-methylphenol

Product 1

HCID 66891782HCID 66891782, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 4-[1-(4-bromophenyl)-1-ethylpropyl]-2-methylphenol (2.1 g, 6.3 mmol) in anhyd MeCN (30 mL) added anhyd K2CO3 (2.9 g, 21 mmol) and benzyl bromide (0.83 mL, 7.0 mmol). The reaction mixture was heated at reflux. After 20 h, the reaction mixture was cooled, diluted with Et2O (100 mL) and filtered. The filtrate was washed with H2O (2×50 mL) and brine, dried (anhyd Na2SO4), concentrated under reduced pressure and chromatographed (silica, EtOAC/Hex, 0:100 to 15:85) to give 5-[1-(4-bromophenyl)-1-ethylpropyl]-2-benzyloxytoluene (2.2 g, 82%), as a colorless liquid: 1H-NMR (CDCl3) δ 7.43-7.48 (2H, m), 7.31-7.42 (5H, m), 7.06 (2H, d, J=8.6), 6.94 (1H, dd, J=2.3, 8.3), 6.89 (1H, d, J=2.3), 6.79 (1H, d, J=8.3), 5.05 (2H, s), 4.23 (1H, s), 2.23 (3H, s), 2.05 (4H, q, J=7.3), 0.62 (6H, t, J=7.3).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux
  3. temperaturethe reaction mixture was cooled
  4. filtrationfiltered
  5. washThe filtrate was washed with H2O (2×50 mL) and brine
  6. dry with materialdried (anhyd Na2SO4)
  7. concentrationconcentrated under reduced pressure
  8. customchromatographed (silica, EtOAC/Hex, 0:100 to 15:85)

Sources & evidence

ORD record
ord-a41bd7aad36f45e88beab39b1c4c1640
Source dataset
uspto-grants-2011_01
Patent number
US07863298B2

Reaction notes

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