Triethylamine → 2,4-difluorophenyl ethyl carbonate

HRID 2042034Notes

Reaction equation

HRID 2042034 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C(N(CC)CC)C.Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19].C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:18](=[O:19])([O:20][CH2:21][CH3:22])[O:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 1230512,4-DifluorophenolHCID 516892Sodium Bicarbonate

Product 1

HCID 111381412,4-difluorophenyl ethyl carbonateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,4-difluorophenol (2 g, 15.4 mmol) in CH2Cl2 (20 mL) was added triethyl amine (3.21 ml, 23 mmol) and ethyl chloroformate (1.77 ml, 18.4 mmol) at 0° C. After stirring the mixture for 1 h at RT, sat. NaHCO3 solution (30 mL) was added, the organic layer was separated and the aqueous layer was extracted with CH2Cl2 (1×25 ml). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated to afford 2,4-difluorophenyl ethyl carbonate (3.11 g, 100% yield) as a liquid.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with CH2Cl2 (1×25 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-921c478c60174f18b49c2b626d0bb460
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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