HCID 53709988, compound → HCID 54382277, compound

HRID 2256970Notes

Reaction equation

HRID 2256970 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[Cl:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([F:24])[C:14]=1[CH:25]([OH:27])[CH3:26]>ClCCl>[Cl:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([F:24])[C:14]=1[C:25](=[O:27])[CH3:26]

Participants

4

Reactant 2

HCID 53709988HCID 53709988, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 54382277HCID 54382277, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridinium chlorochromate (27.6 g) was suspended in dichloromethane and ethyl 4-chloro-2-fluoro-3-(1-hydroxyethyl)benzoate (14.1 g) was added. The mixture was stirred at room temperature for 2 hours and then heated at reflux for 2 hours. After cooling the solvent was evaporated and the residue purified by column chromatography eluted with a mixture of ethyl acetate and n-hexane (1:5) to give ethyl 4-chloro-3-acetyl-2-fluorobenzoate as a yellow oil (13 g), NMR (CDCl3) 1.3(t,3H), 2.5(s,3H), 4.3(q,2H), 7.1(d,1H), 7.8(t,1H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperatureAfter cooling the solvent
  4. customwas evaporated
  5. customthe residue purified by column chromatography
  6. washeluted with a mixture of ethyl acetate and n-hexane (1:5)

Sources & evidence

ORD record
ord-909b5708017545c285185659773ea723
Source dataset
uspto-grants-1997_08
Patent number
US05656573

Reaction notes

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