2-Fluorophenol → HCID 21186647, compound

HRID 1384314Notes

Reaction equation

HRID 1384314 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5](Cl)(=[O:8])[CH2:6][CH3:7].[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17]>C(Cl)Cl>[C:5]([O:17][C:12]1[CH:13]=[CH:14][C:15]([C:5](=[O:8])[CH2:6][CH3:7])=[CH:16][C:11]=1[F:10])(=[O:8])[CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 97072-FluorophenolHCID 62324Propionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 21186647HCID 21186647, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of aluminum chloride (45.8 g, 0.343 mol) in methylene chloride (140 mL) was added propionyl chloride (10.85 mL, 124.9 mmol) all at once followed by 2-fluorophenol (5.57 mL, 62.44 mmol in 25 mL of methylene chloride with a 10 mL rinse). The mixture was gently refluxed 5 h, cooled to ambient temperature and poured onto ice. The phases were separated and the aqueous layer was extracted with methylene chloride. The combined organic layer was washed with aqueous bicarbonate and brine. The organic layer was dried over calcium sulfate and concentrated to give 11.43 g (82%) of 4-propionyl-2-fluorophenyl propionate as a clear tan oil which was used without characterization.

Workup

  1. washrinse)
  2. additionpoured onto ice
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with methylene chloride
  5. washThe combined organic layer was washed with aqueous bicarbonate and brine
  6. dry with materialThe organic layer was dried over calcium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b8461f21639541ba9619fbea4cda902b
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

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