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

HRID 857357Notes

Reaction equation

HRID 857357 reaction equation
[Br:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:11][O-:12].[Na+].CO>CO.C(Cl)Cl.O>[Br:1][C:2]1[CH:9]=[C:8]([O:12][CH3:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 2

HCID 27733192-Bromo-4-fluorobenzaldehydeHCID 23694274Sodium methanolate methanol

Product 1

HCID 111276412-Bromo-4-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21908982Water methylene chlorideSolvent

Procedure

To a solution of 2-bromo-4-fluorobenzaldehyde (50 g, 246 mmol), in MeOH (500 mL) in a 15° C. water bath was added a 25% solution of NaOMe/MeOH (88 mL). The mixture was stirred at r.t. for 1 hour followed by 2 hours at reflux. The solid was filtered and the filtrate was concentrated to dryness to give a second crop of solid. Both crops were taken up in CH2Cl2/H2O. After washing with H2O, the organic phase was dried (MgSO4), filtered, and evaporated to give an off-white solid (52.2 g).

Workup

  1. waitfollowed by 2 hours
  2. temperatureat reflux
  3. filtrationThe solid was filtered
  4. concentrationthe filtrate was concentrated to dryness
  5. customto give a second crop of solid
  6. washAfter washing with H2O
  7. dry with materialthe organic phase was dried (MgSO4)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-4eff59624f9a47a0aac51d081ec53409
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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