1,3-Dibromo-5-fluorobenzene → 3,5-Dibromoanisole

HRID 1371493Notes

Reaction equation

HRID 1371493 reaction equation
[CH3:1][O-:2].[Na+].[Br:4][C:5]1[CH:6]=[C:7](F)[CH:8]=[C:9]([Br:11])[CH:10]=1>CN(C)C=O>[Br:4][C:5]1[CH:6]=[C:7]([O:2][CH3:1])[CH:8]=[C:9]([Br:11])[CH:10]=1

Participants

4

Procedure

Sodium methoxide (4.5M solution in methanol, 8.80 ml, 41.0 mmol) was added dropwise to a stirred solution of 3,5-dibromofluorobenzene (5.00 g, 19.0 mmol) in N,N-dimethylformamide (95 ml) at 0° C. under a nitrogen atmosphere. The reaction was warmed to room temperature, stirred for 1 hour and then evaporated under reduced pressure. The residue was dissolved in diethyl ether and was washed with water (3×300 ml) and brine (300 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure to give the title compound as a white solid (5.13 g).

Workup

  1. customevaporated under reduced pressure
  2. dissolutionThe residue was dissolved in diethyl ether
  3. washwas washed with water (3×300 ml) and brine (300 ml)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b8081fcc32434992b1d8627662587f5e
Source dataset
uspto-grants-2007_01
Patent number
US07157468B2

Reaction notes

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