Iodoethane → HCID 18349302, compound

HRID 2268112Notes

Reaction equation

HRID 2268112 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:3]=1[OH:16].[H-].[Na+].[H][H].[CH2:21](I)[CH3:22]>CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:9])([CH3:10])[CH3:11])[CH:5]=[C:4]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:3]=1[O:16][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 5198222-Bromo-4,6-di-tert-butylphenolHCID 178418361HCID 178418361, compound

Product 1

HCID 18349302HCID 18349302, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of 13 g of 2-bromo-4,6-di-tert.butyl-phenol in 100 ml of dimethylformamide (DMF) was added dropwise to a suspension of 2.2 g of sodium hydride (50% in mineral oil) in 100 ml of DMF at 0° C. The reaction mixture was stirred at room temperature until hydrogen was no longer evolved (ca. 1 h), cooled again to 0° C. and treated with a solution of 22 g of ethyl iodide in 50 ml of DMF. After stirring for about 1 hour at room temperature, the reaction mixture was poured on icewater, extracted with ethyl acetate, washed (H2O), dried (Na2SO4) and evaporated to give 13.5 g of 1-bromo-2-ethoxy-3,5-di-tert.butyl-benzene as white crystals, m.p. 55-56° C.

Workup

  1. custom(ca. 1 h)
  2. additionthe reaction mixture was poured on icewater
  3. extractionextracted with ethyl acetate
  4. washwashed (H2O)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-0d465c908e0d48cba70957222406356e
Source dataset
uspto-grants-2001_12
Patent number
US06326397B1

Reaction notes

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