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

HRID 1054848Notes

Reaction equation

HRID 1054848 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 97.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of 4-bromo-2-fluorobenzaldehyde (6.1 g, 0.03 mol) and sodium methoxide (1.78 g, 0.033 mol) in dry methanol (60 mL) was stirred at reflux for 16 hours. The methanol was evaporated. The residue was partitioned between DCM and water. The organic layers were dried over sodium sulfate, concentrated in vacuo to give a yellow solid, which was purified by silica gel chromatography (Petroleum ether/EtOAc=20:1 to 10:1) to give the title compound (6.3 g, 97%) as a light yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 10.23 (s, 1H), 7.60 (d, 1H), 7.48 (s, 1H), 7.28 (d, 1H), 3.94 (s, 3H)

Workup

  1. temperatureat reflux for 16 hours
  2. customThe methanol was evaporated
  3. customThe residue was partitioned between DCM and water
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a yellow solid, which
  7. customwas purified by silica gel chromatography (Petroleum ether/EtOAc=20:1 to 10:1)

Sources & evidence

ORD record
ord-164a4f009f6d4eb0bca121b96e64cf7b
Source dataset
uspto-grants-2016_07
Patent number
US09394285B2

Reaction notes

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