Hydrochloric Acid → HCID 66858654, compound

HRID 1803149Notes

Reaction equation

HRID 1803149 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[F:7][C:8]1[C:13]([F:14])=[CH:12][CH:11]=[CH:10][C:9]=1[OH:15].C(N(CC)CC)C.Cl>CCOC(C)=O>[C:2](=[O:3])([O:4][CH2:5][CH3:6])[O:15][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]([F:14])[C:8]=1[F:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 808792,3-Difluorophenol

Product 1

HCID 66858654HCID 66858654, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Step M (1): Ethyl chloroformate (16.6 g, 153 mmol) was added to a solution of 2,3-difluorophenol (20 g, 153 mmol) and triethylamine (20.7 mL, 146 mmol) in EtOAc (200 mL). The resulting mixture was stirred at rt for 2 h. The crude reaction was poured into 1 N HCl and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified using silica gel column chromatography (5% EtOAc/hexane) to afford 2,3-difluorophenyl ethyl carbonate (20 g, 64% yield).

Workup

  1. customThe crude reaction
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified

Sources & evidence

ORD record
ord-862ab532795748cb80fd783f06c702c2
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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