4-Bromo-2-fluorobenzaldehyde → 4-Bromo-2-methoxybenzaldehyde

HRID 1047972Notes

Reaction equation

HRID 1047972 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4](F)[CH:3]=1.[CH3:11][O-:12].[Na+]>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:12][CH3:11])[CH:3]=1

Participants

4

Reactant 2

HCID 1435174-Bromo-2-fluorobenzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 110530414-Bromo-2-methoxybenzaldehydeYield 61.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-bromo-2-fluorobenzaldehyde (3.38 g; 16 mmol) in 35 mL methanol at ambient temperature was added sodium methoxide solution (4.0 mL of 25% solution; 17.6 mmol), and the resulting solution was stirred and heated to reflux. After refluxing for 2 hours the solvent was evaporated. The residue was partitioned between 100 mL dichloromethane and 50 mL water. The organic layer was dried over sodium sulfate and evaporated. The residue was purified by silica gel chromatography to give 2.13 g of 4-bromo-2-methoxybenzaldehyde as a white solid. MS (apci, neg) m/z=199.

Workup

  1. temperatureheated to reflux
  2. temperatureAfter refluxing for 2 hours the solvent
  3. customwas evaporated
  4. customThe residue was partitioned between 100 mL dichloromethane and 50 mL water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f32e2f6262ad472b83f2b5db22086448
Source dataset
uspto-grants-2013_10
Patent number
US08569522B2

Reaction notes

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