1-Bromo-3,5-difluorobenzene → 3-Bromo-5-fluoroanisole

HRID 1666468Notes

Reaction equation

HRID 1666468 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[C:4]([F:9])[CH:3]=1.[CH3:10][O-:11].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([O:11][CH3:10])[CH:5]=[C:4]([F:9])[CH:3]=1

Participants

4

Reactant 2

HCID 1363131-Bromo-3,5-difluorobenzeneHCID 10942334Sodium Methoxide

Product 1

HCID 108220943-Bromo-5-fluoroanisoleYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-bromo-3,5-difluorobenzene (10 g, 0.052 mol) in dry DMF (300 mL) cooled to 0-5° C. was added sodium methoxide (5.60 g, 0.1036 mol) and the reaction mixture was stirred at RT for 24 h. The reaction mixture was extracted with ethyl acetate three times. The organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness to give the title compound (7.5 g, 71%).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate three times
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-b76982e8978745dc8ead151f36cd78bb
Source dataset
uspto-grants-2011_10
Patent number
US08044052B2

Reaction notes

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