Dimethylformamide → 1-Bromo-4-(methoxymethoxy)benzene

HRID 1940983Notes

Reaction equation

HRID 1940983 reaction equation
[CH:1]1[C:6]([OH:7])=[CH:5][CH:4]=[C:3]([Br:8])[CH:2]=1.CN(C)C=O.[H-].[Na+].[CH3:16][O:17][CH2:18]Cl>O>[CH3:16][O:17][CH2:18][O:7][C:6]1[CH:5]=[CH:4][C:3]([Br:8])=[CH:2][CH:1]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78084-BromophenolHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydride

Product 1

HCID 104659191-Bromo-4-(methoxymethoxy)benzeneYield 79.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

Into a reactor, 40 g of p-bromophenol and 200 ml of DMF (dimethylformamide) were charged, to which 10 g of a 60% NaH (sodium hydride) were gradually added to give a solution. To the solution, 18 g of methoxymethyl chloride were added dropwise with stirring at a temperature of 30° C. or lower, and reacted overnight at room temperature to give a reaction solution. The reaction solution was poured into water, extracted with benzene, washed with water, dried over sodium sulfate anhydride, and thereafter the solvent was evaporated and the residue was distilled under reduced pressure to give 38.4 g (Y., 79.3%) of 4-bromopheny methoxymethyl ether.

Workup

  1. additionwere gradually added
  2. customto give a solution
  3. customlower, and reacted overnight at room temperature
  4. customto give a reaction solution
  5. extractionextracted with benzene
  6. washwashed with water
  7. dry with materialdried over sodium sulfate anhydride
  8. customthe solvent was evaporated
  9. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-5fba03db5b2c4a03a9270cefe6636e3b
Source dataset
uspto-grants-1997_12
Patent number
US05702642

Reaction notes

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