2-Bromo-4-hydroxymethylphenol → (3-Bromo-4-methoxyphenyl)methanol

HRID 1018705Notes

Reaction equation

HRID 1018705 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH2:5][OH:6].[CH3:11][O-].[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 1215942-Bromo-4-hydroxymethylphenolHCID 10942334Sodium Methoxide

Product 1

HCID 13551346(3-Bromo-4-methoxyphenyl)methanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Bromo-4-hydroxybenzyl alcohol (1.22 g, 6.0 mmol) prepared from i) and sodium methoxide (0.36 g, 6.6 mmol) as base were added to N,N-dimethylformamide (100 ml), and the mixture was stirred for 30 min at room temperature. Chloromethyl resin (Merrifield resin, 1 mmol of chloromethyl site, formula 4; 1.22 g, 2.0 mmol) was added to the reaction solution and stirred for 24 hr at 50° C. The same was filtrated and washed repeatedly with water, methanol and dichloromethane. IR and XPS analyses were performed.

Workup

  1. stirringstirred for 24 hr at 50° C
  2. filtrationThe same was filtrated
  3. washwashed repeatedly with water, methanol and dichloromethane

Sources & evidence

ORD record
ord-65a5cf7d326a4c8bbea1083166b40ca6
Source dataset
uspto-grants-2002_11
Patent number
US06482898B1

Reaction notes

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