p-Toluenesulfonic acid monohydrate → HCID 59216307, compound

HRID 500136Notes

Reaction equation

HRID 500136 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([C:12](=[O:15])[CH:13]=[O:14])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C([O-])([O-])[O:17][CH2:18][CH3:19].O.[C:23]1(C)C=CC(S(O)(=O)=O)=C[CH:24]=1>C1(C)C=CC=CC=1>[CH2:23]([O:14][CH:13]([O:17][CH2:18][CH3:19])[C:12]([C:10]1[CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([F:1])[CH:11]=1)=[O:15])[CH3:24]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 53630039EthylorthoformateHCID 59216303Methyl 2-fluoro-4-(oxoacetyl)benzoate

Product 1

HCID 59216307HCID 59216307, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of methyl 2-fluoro-4-(oxoacetyl)benzoate (6.0 g, 0.028 mol), ethyl orthoformate (12.0 mL, 0.071 mol), and p-toluenesulfonic acid monohydrate (200 mg) in toluene (60 mL) was heated under reflux for 4 h. After cooling, the reaction mixture was concentrated under reduced pressure to give the desired product which was used in the next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 h
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-74b159bc31614c3ea9495272657712e7
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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