Water → 5-Fluoro-2-methoxy-4-nitrobenzaldehyde

HRID 1667783Notes

Reaction equation

HRID 1667783 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].IC.[F:9][C:10]1[C:11]([N+:19]([O-:21])=[O:20])=[CH:12][C:13](O)=[C:14]([CH:17]=1)[CH:15]=[O:16].O>CN(C)C=O>[F:9][C:10]1[C:11]([N+:19]([O-:21])=[O:20])=[CH:12][C:13]([O:4][CH3:1])=[C:14]([CH:17]=1)[CH:15]=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86642844HCID 86642844, compound

Product 1

HCID 862228455-Fluoro-2-methoxy-4-nitrobenzaldehydeYield 94.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.524 g (3.80 mmole) of potassium carbonate, 0.5 mL of iodomethane and 8 mL of dimethylformamide was added, dropwise, a solution of 0.141 g (0.76 mmole) of 5-fluoro-2-hydroxy-4-nitro-benzaldehyde (IV.46b) in 1 mL of dimethylformamide. The resulting dark red solution was stirred at room temperature for 3 hours. The mixture was poured into 50 mL of water and extracted three times with 25 mL of ethyl acetate. The combined organic layers were washed three times with 25 mL of water, once with 25 mL of brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.143 g of 5-fluoro-2-methoxy-4-nitro-benzaldehyde (IV.46c) as a yellow solid.

Workup

  1. additionwas added
  2. extractionextracted three times with 25 mL of ethyl acetate
  3. washThe combined organic layers were washed three times with 25 mL of water
  4. dry with materialonce with 25 mL of brine, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-049f13a8dbed4e36868cf11efc03d0c2
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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