Isopropyl iodide → 4-Bromo-2-ethyl-1-isopropoxybenzene

HRID 1453233Notes

Reaction equation

HRID 1453233 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH:8]([CH3:10])[CH3:9].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH2:19][CH3:20])[CH:13]=1>CN(C=O)C>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH:8]([CH3:10])[CH3:9])=[C:14]([CH2:19][CH3:20])[CH:13]=1

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 878774-Bromo-2-ethylphenol

Product 1

HCID 587624584-Bromo-2-ethyl-1-isopropoxybenzeneYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (3.1 g, 22.4 mmol) followed by 2-iodopropane (0.75 mL, 7.5 mmol) were added to a solution of 4-bromo-2-ethyl-phenol (1.5 g, 7.5 mmol) in DMF (10 mL). The mixture was heated at 60° C. for 20 hours and then partitioned between 1N HCl and EtOAc. The organic layers were washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The crude yellow oil was purified by flash column chromatography (hexanes) to give the desired product (1.35 g, 75%). 1H NMR (400 MHz, CDCl3): δ 1.16 (t, J=7.6 Hz, 3H), 1.32 (d, J=6.1 Hz, 6H), 2.58 (q, J=7.6 Hz, 2H), 4.49 (m, 1H), 6.70 (d, J=8.6 Hz, 1H), 7.23 (m, 2H).

Workup

  1. custompartitioned between 1N HCl and EtOAc
  2. washThe organic layers were washed with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe crude yellow oil was purified by flash column chromatography (hexanes)

Sources & evidence

ORD record
ord-e596aaddeaec4f11adceb0bd7e85c42a
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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