Iodoethane → Methyl 4-ethoxy-3-fluorobenzoate

HRID 1386943Notes

Reaction equation

HRID 1386943 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([F:11])[CH:5]=1.C([O-])([O-])=O.[K+].[K+].[CH2:19](I)[CH3:20].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:19][CH3:20])=[C:6]([F:11])[CH:5]=1

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 7019368Methyl 3-fluoro-4-hydroxybenzoate

Product 1

HCID 69830438Methyl 4-ethoxy-3-fluorobenzoateYield 101%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-fluoro-4-hydroxy-benzoic acid methyl ester (1.5 g, 8.82 mmol), K2CO3 (2.43 g, 17.6 mmol) and ethyliodide (2.75 g, 17.6 mmol) in DMF (15 ml) was heated to 80° C. for 2 hrs. Addition of excess Na2CO3 and extraction with EtOAc followed by washing with satd. NaCl, then drying with Na2SO4 and evaporation afforded the title compound (1.76 g, 101% yield) as an orange oil. MS: m/e=170 (M+).

Workup

  1. washby washing with satd
  2. dry with materialNaCl, then drying with Na2SO4 and evaporation

Sources & evidence

ORD record
ord-2a5a687c0fb846e382d875a5eeb02a07
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

Loading…