Water → 1,1'-[(4-Bromo-1,3-phenylene)bis(oxymethylene)]dibenzene

HRID 1049395Notes

Reaction equation

HRID 1049395 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][C:3]=1O.[C:10](=[O:13])([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O>CN(C=O)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([O:6][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:4][C:3]=1[O:13][CH2:10][C:2]1[CH:8]=[CH:7][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 811054-Bromoresorcinol

Product 1

HCID 128821681,1'-[(4-Bromo-1,3-phenylene)bis(oxymethylene)]dibenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromoresorcinol (10.0 g) and potassium carbonate (21.9 g) in DMF (100 mL) was added benzyl bromide (13.2 mL), and the mixture was stirred at room temperature for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (21.8 g) as a crude oil. This compound was used for the next step without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-71ceb44d36f4475c9258aae541654eff
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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