Chloromethyl Methyl Ether → 4-Bromo-2-fluoro-1-methoxymethoxy-benzene

HRID 1959960Notes

Reaction equation

HRID 1959960 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([F:9])[CH:3]=1.[CH3:10][O:11][CH2:12]Cl.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][O:11][CH3:12])=[C:4]([F:9])[CH:3]=1

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenol

Product 1

HCID 220320154-Bromo-2-fluoro-1-methoxymethoxy-benzeneYield 98.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into acetone (300 ml), 4-bromo-2-fluorophenol (30 g, 157 mmol) was dissolved, to which chloromethyl methyl ether (18 ml, 237 mmol) and potassium carbonate (43 g, 235 mmol) were added, followed by stirring at room temperature for two hours. Impurities were filtered off and the filtered solution was washed with acetone. The filtrate was concentrated under reduced pressure and the residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-85:15, V/V) to give the desired title compound (36.5 g, yield 82%).

Workup

  1. additionwere added
  2. filtrationImpurities were filtered off
  3. washthe filtered solution was washed with acetone
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue thus obtained
  6. customwas purified by silica gel column chromatography (hexane:ethyl acetate, 100:0-85:15, V/V)

Sources & evidence

ORD record
ord-6afd9f62e9604810a203260111438fc7
Source dataset
uspto-grants-2013_04
Patent number
US08410273B2

Reaction notes

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