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

HRID 338516

Reaction equation

HRID 338516 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-f10ddf9e31c6467c9c7d5611ebcdeb79
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Linked notes

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