4-Chloro-2-fluorobenzaldehyde → 4-Chloro-2-methoxybenzaldehyde

HRID 1021459Notes

Reaction equation

HRID 1021459 reaction equation
[Cl: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+]>>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([O:12][CH3:11])[CH:3]=1

Participants

3

Reactant 2

HCID 27249084-Chloro-2-fluorobenzaldehydeHCID 10942334Sodium Methoxide

Product 1

HCID 138651154-Chloro-2-methoxybenzaldehydeYield 77.8%

Conditions

Temperature
50 °C

Procedure

4-Chloro-2-Fluorobenzaldehyde (300 mg, 1.89 mmol) was diluted with NaOMe (3784 μL, 1.89 mmol) (solution in methanol), heated to 50° C. and stirred for 3 hours. The reaction was concentrated in half and loaded directly onto a biotage 25 cartridge eluting with 5% ethyl acetate/hexanes to yield 4-chloro-2-methoxybenzaldehyde (250 mg, 1.47 mmol, 77.5% yield).

Workup

  1. concentrationThe reaction was concentrated in half
  2. washeluting with 5% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b7ce37215e8e44b897711a6a11f22e37
Source dataset
uspto-grants-2014_05
Patent number
US08716498B2

Reaction notes

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