Iodoethane → o-Fluorophenatole

HRID 1908134Notes

Reaction equation

HRID 1908134 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].I[CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:10]([O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[CH3:11]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 97072-FluorophenolHCID 11430Potassium Carbonate

Product 1

HCID 136291o-FluorophenatoleYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-fluorophenol (8.6 g, 77 mmol), iodoethane (9.2 mL, 120 mmol) and potassium carbonate (21 g, 150 mmol) (finely powdered) was stirred in acetone (100 mL) at 50° C. overnight, then at room temperature for 24 h. The mixture was filtered over a pad of silica gel, and was rinsing with ether. The solution was carefully concentrated (due to volatility of product), then microfiltered to give 1-ethoxy-2-fluoro-benzene (92%) as a yellow oil. 1H NMR (CDCl3, 500 MHz), δ 7.12-6.94 (m, 2H), 6.91-6.86 (m, 1H), 6.83-6.77 (m, 1H), 4.01 (q, J=7.0 Hz, 2H), 1.37 (t, J=7.0 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered over a pad of silica gel
  2. washwas rinsing with ether
  3. concentrationThe solution was carefully concentrated (due to volatility of product)

Sources & evidence

ORD record
ord-fe8a8d5b63354ffea66ea838705ef553
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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