3,4,5-Trifluorophenol → 3,4,5-Trifluorophenyl 4-(2-methoxyethoxy)benzoate

HRID 747073Notes

Reaction equation

HRID 747073 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([F:9])[C:7]=1[F:8].[CH3:11][O:12][CH2:13][CH2:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1>ClCCl.CN(C)C1C=CN=CC=1>[CH3:11][O:12][CH2:13][CH2:14][O:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([O:10][C:4]2[CH:3]=[C:2]([F:1])[C:7]([F:8])=[C:6]([F:9])[CH:5]=2)=[O:21])=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 27779433,4,5-TrifluorophenolHCID 64855624-(2-Methoxyethoxy)benzoic acid

Product 1

HCID 693012783,4,5-Trifluorophenyl 4-(2-methoxyethoxy)benzoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3,4,5-trifluorophenol (0.38 g, 2.55×10−3 mol) in dichloromethane (10 cm3) was added to a solution of N,N-dicyclohexylcarbodiimide (0.63 g, 3.06×10−3 mol), 4-(2-methoxyethoxy)benzoic acid (0.50 g, 2.55×10−3 mol), 4-(dimethylamino)pyridine (0.03 g 2.55×10−4mol) in dichloromethane (5 cm3), at 0° C. and then left to stirred overnight, filtered to remove precipitated material (DCU) and the filtrate evaporated down under reduced pressure. The crude product was purified by column chromatography on silica gel using a 1:1 dichloromethane-petroleum ether (40°-60° C.) mixture as eluent, followed by recrystalisation from ethanol. Yield 0.32 g (38%), GC purity (99.76%).

Workup

  1. waitleft
  2. filtrationfiltered
  3. customto remove
  4. customprecipitated material (DCU)
  5. customthe filtrate evaporated down under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel using a 1:1 dichloromethane-petroleum ether (40°-60° C.) mixture as eluent
  7. customfollowed by recrystalisation from ethanol

Sources & evidence

ORD record
ord-623214c806a24cb2a148660192ed5eb8
Source dataset
uspto-grants-2008_07
Patent number
US07396487B2

Reaction notes

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