Ethyl Bromide → 1-(4-Ethoxy-2-methylphenyl)-2,5-dimethyl-1H-pyrrole

HRID 2375377Notes

Reaction equation

HRID 2375377 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[CH3:14])=[C:4]([CH3:15])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH3:24]>C(#N)C>[CH3:14][C:9]1[N:8]([C:5]2[CH:6]=[CH:7][C:2]([O:1][CH2:23][CH3:24])=[CH:3][C:4]=2[CH3:15])[C:12]([CH3:13])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 230083314-(2,5-Dimethyl-1H-pyrrol-1-yl)-3-methylphenol

Product 1

HCID 692752351-(4-Ethoxy-2-methylphenyl)-2,5-dimethyl-1H-pyrrole

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 1-(4-hydroxy-2-methylphenyl)-2,5-dimethylpyrrole (˜50 mmol) in acetonitrile (300 mL) was added potassium carbonate (55 mmol) and an excess of bromoethane (>100 mmol). The reaction mixture was stirred at 50° C. overnight, cooled to room temperature, and partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4, filtered, concentrated in vacuo, and purified by column chromatography (15% EtOAc/hexanes) to give 2,5-dimethyl-1-(4-ethoxy-2-methylphenyl)pyrrole as a colorless oil: 1H NMR (CDCl3, 500 MHz) δ 7.07 (d, 1H), 6.84 (d, 1H), 6.79 (dd, 1H), 5.90 (s, 2H), 4.07 (q, 2H), 1.92 (s, 6H), 1.90 (s, 3H), 1.45 (t, 3H; MS (ESI) 230 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. custompartitioned between EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-5c26fd148e86407ba61481101872bcbb
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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