Iodoethane → 4-Bromophenetole

HRID 1063895Notes

Reaction equation

HRID 1063895 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:15](I)[CH3:16]>CN(C)C=O>[CH2:15]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[CH3:16]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 78084-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 685234-Bromophenetole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 4-bromophenol (5.00 g) and potassium carbonate (5.99 g) in anhydrous dimethylformamide (25 ml) was added ethyl iodide (2.77 ml) under ice-water cooling and the mixture was stirred at 0° C. for 2 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with 2N aqueous sodium hydroxide solution, water and brine, dried over magnesium sulfate, and evaporated in vacuo to give 4-ethoxybromobenzene as yellow oil (5.44 g).

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with 2N aqueous sodium hydroxide solution, water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-b4c5625f539445e199b1c4e71dc13215
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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