Hydrochloric Acid → Methyl 3-fluoro-4-formylbenzoate

HRID 2233057Notes

Reaction equation

HRID 2233057 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH:13]=[O:14])[C:7]([OH:9])=[O:8].[CH3:15]I.Cl>CN(C=O)C>[CH3:15][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:12]([CH:13]=[O:14])=[C:4]([F:3])[CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 212845583-Fluoro-4-formylbenzoic acid

Product 1

HCID 18766342Methyl 3-fluoro-4-formylbenzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

60% NaH (0.14 mol) is added portionwise to a solution of 3-fluoro-4-formyl benzoic acid (3, 0.12 mol) in dry DMF (330 mL). The mixture is stirred at room temperature for 30 min. Methyl iodide (0.14 mol) is added dropwise to the mixture. After stirring at room temperature for 5 h, the reaction mixture is poured into 1 N HCl (ca. 1000 mL) and extracted twice with EtOAc. The combined organic layers are washed with saturated aqueous NaHCO3, brine, dried over MgSO4, and evaporated in vacuo to give crude 3-fluoro-4-formyl benzoic acid methyl ester (4).

Workup

  1. stirringAfter stirring at room temperature for 5 h
  2. extractionextracted twice with EtOAc
  3. washThe combined organic layers are washed with saturated aqueous NaHCO3, brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-eb3b4645849e44f5a76852583bc8f0ba
Source dataset
uspto-grants-2010_05
Patent number
US07709470B2

Reaction notes

Loading…