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

HRID 1054860Notes

Reaction equation

HRID 1054860 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 94.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-bromo-2-fluorobenzaldehyde (25.0 g, 0.123 mol) and sodium methoxide (13.99 g, 0.2600 mol) in dry methanol (250 mL) was stirred at reflux temperature for 16 hours. The mixture was concentrated and the residue was partitioned between dichloromethane (500 mL) and water (250 mL). The organic layers were combined and dried over sodium sulfate then concentrated in vacuo to provide the title compound as yellow solid (25 g, 94.5%).

Workup

  1. temperatureat reflux temperature for 16 hours
  2. concentrationThe mixture was concentrated
  3. customthe residue was partitioned between dichloromethane (500 mL) and water (250 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-c03fb3f840b34d3babe72134652dc9fd
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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