4-Bromophenol → HCID 22132756, compound

HRID 1857115Notes

Reaction equation

HRID 1857115 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:11][O:12][CH2:13]Cl>CN(C)C=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:11][O:12][CH3:13])([OH:8])[CH2:4][CH:3]=1

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydride

Product 1

HCID 22132756HCID 22132756, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Commercially available 4-bromophenol (17.3 g) was dissolved in N,N-dimethylformamide (90 ml), to which sodium hydride (2.64 g) was added while cooled in ice. After stirring at room temperature overnight, chloromethyl methyl ether (8.35 ml) was added, and the admixture was stirred for a further 1 hour. The reaction mixture was partitioned between water and ethyl acetate, and the ethyl acetate layer was dried with anhydrous magnesium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by column chromatography on silica gel eluting with hexane/acetone to obtain 18.25 g of the title compound (yield: 84%).

Workup

  1. additionwas added
  2. temperaturewhile cooled in ice
  3. stirringthe admixture was stirred for a further 1 hour
  4. customThe reaction mixture was partitioned between water and ethyl acetate
  5. dry with materialthe ethyl acetate layer was dried with anhydrous magnesium sulfate
  6. customAfter removing the solvent
  7. distillationby reduced-pressure distillation
  8. customthe resulting residue was purified by column chromatography on silica gel eluting with hexane/acetone

Sources & evidence

ORD record
ord-7dfbe84f52904dfd86683bd554c94883
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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