Water → O-ethoxycarbonyl-2,3,4-trifluorophenol

HRID 1736245Notes

Reaction equation

HRID 1736245 reaction equation
[F:1][C:2]1[C:7]([F:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[OH:10].C(N(CC)CC)C.Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20].O>ClCCl>[CH2:22]([O:21][C:19]([O:10][C:3]1[CH:4]=[CH:5][C:6]([F:9])=[C:7]([F:8])[C:2]=1[F:1])=[O:20])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 1231742,3,4-Trifluorophenol

Product 1

HCID 67566268O-ethoxycarbonyl-2,3,4-trifluorophenolYield 89.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.40 g (50.0 mmol) of 2,3,4-trifluorophenol was dissolved in 50 mL of dichloromethane, 8.30 mL (60.0 mmol) of triethylamine and 5.74 mL (60.0 mmol) of ethyl chloroformate were added under ice-cooling and the mixture was stirred at room temperature for 20 minutes. Water was added to the reaction solution and the mixture was extracted once with chloroform. The organic layer was washed once with an aqueous saturated solution of sodium chloride, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give 9.83 g of O-ethoxycarbonyl-2,3,4-trifluorophenol (yield: 89%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted once with chloroform
  3. washThe organic layer was washed once with an aqueous saturated solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b8a89b73649e4a219224766e7b10407a
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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