Dimethylformamide → Ethyl 4-fluoro-2-hydroxybenzoate

HRID 1464184Notes

Reaction equation

HRID 1464184 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([OH:11])[CH:3]=1.[C:12]([O-])(=O)[CH3:13].[Na+].C(I)C.CN(C)C=O>O>[CH2:12]([O:7][C:6](=[O:8])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][C:4]=1[OH:11])[CH3:13]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 676614-Fluorosalicylic acidHCID 517045Sodium Acetate

Product 1

HCID 22478444Ethyl 4-fluoro-2-hydroxybenzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Fluoro-2-hydroxy-benzoic acid (10.8 g, 0.07 mol), sodium acetate (6.9 g, 0.084 mol), ethyl iodide (55 g, 0.35 mol) and dimethylformamide was stirred at ambient temperature for 48 h. The mixture was poured into water and extracted with n-hexane. The solution was filtered through a plug of silica gel and evaporated. The residue was almost pure product and was used directly in the next step. Yield 10.2 g, 80%.

Workup

  1. extractionextracted with n-hexane
  2. filtrationThe solution was filtered through a plug of silica gel
  3. customevaporated

Sources & evidence

ORD record
ord-a96864aa136544a6b87eff8ef5bfce5b
Source dataset
uspto-grants-1994_04
Patent number
US05302718

Reaction notes

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