2-Bromophenol → HCID 22009924, compound

HRID 322062Notes

Reaction equation

HRID 322062 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:15][C:14]1[CH:17]=[CH:18][C:11]([O:10][CH3:9])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chloride

Product 1

HCID 22009924HCID 22009924, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 2-bromophenol (5.19 g), 4-methoxybenzyl chloride (4.70 g), potassium carbonate (4.15 g) and acetone (30 ml) is heated under reflux for 8 hours. The cool mixture is evaporated under reduced pressure, and the residue is mixed with water (60 ml) and ether (60 ml) and shaken. The aqueous layer is extracted with ether (2×60 ml), and the combined extracts washed with 2M sodium hydroxide solution (20 ml) and water (20 ml), dried (MgSO4) and evaporated to give a solid residue which is recrystallized from ethanol to give 6.18 g of 1-bromo-2-(4-methoxybenzyloxy)benzene, mp 87-90° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 8 hours
  3. customThe cool mixture is evaporated under reduced pressure
  4. additionthe residue is mixed with water (60 ml) and ether (60 ml)
  5. extractionThe aqueous layer is extracted with ether (2×60 ml)
  6. washthe combined extracts washed with 2M sodium hydroxide solution (20 ml) and water (20 ml)
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customto give a solid residue which
  10. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-ebb43cde328f41518130e93cb6eee1b7
Source dataset
uspto-grants-2001_04
Patent number
US06211220B1

Reaction notes

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