Iodoethane → 3-Bromo-4-ethoxybenzyl alcohol

HRID 1888767Notes

Reaction equation

HRID 1888767 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[OH:10].I[CH2:12][CH3:13].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][C:3]=1[O:10][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 1215942-Bromo-4-hydroxymethylphenol

Product 1

HCID 580476873-Bromo-4-ethoxybenzyl alcoholYield 87.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-bromo-4-(hydroxymethyl)phenol (3.00 g, 14.7 mmol), iodoethane (4.60 mL, 44.3 mmol) and potassium carbonate (6.12 g, 44.3 mmol) in ethanol (30 mL) was stirred at room temperature for 2 days. The obtained reaction mixture was filtered through celite, and the solvent was evaporated under reduced pressure. The residue was applied to silica gel chromatography (ethyl acetate). The solvent was evaporated under reduced pressure to give (3-bromo-4-ethoxyphenyl)methanol (2.98 g) as a white solid.

Workup

  1. customThe obtained reaction mixture
  2. filtrationwas filtered through celite
  3. customthe solvent was evaporated under reduced pressure
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-825de0de19a44d139f4af8e76ce0f888
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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