Water → 2,5-Difluoro-4-(pyrrol-1-yl)benzoic acid

HRID 4569Notes

Reaction equation

HRID 4569 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([NH2:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].CO[C:15]1(OC)[CH2:19][CH2:18][CH2:17]O1.O>C(O)(=O)C>[F:1][C:2]1[CH:10]=[C:9]([N:11]2[CH:15]=[CH:19][CH:18]=[CH:17]2)[C:8]([F:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 11788317dimethoxytetrahydrofuraneHCID 201514774-Amino-2,5-difluorobenzoic acid

Product 1

HCID 201514742,5-Difluoro-4-(pyrrol-1-yl)benzoic acidYield 79.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5.2 grams (0.03 mol) of 2,5-difluoro-4-aminobenzoic acid, melting at 250°-3°, are dissolved in 60 ml of glacial acetic acid, and 4 grams (0.03 mol) of dimethoxytetrahydrofuran are added. The mixture is heated at the boil for 10 minutes, 20 ml of water are added and the resulting mixture is left to cool. The precipitate formed is filtered off and washed with water to give 5.3 grams of a solid melting at 196°-8° C.

Workup

  1. temperatureThe mixture is heated at the boil for 10 minutes
  2. waitthe resulting mixture is left
  3. temperatureto cool
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washwashed with water

Sources & evidence

ORD record
ord-dc223d62d465498286c60c57753211e7
Source dataset
uspto-grants-1988_02
Patent number
US04727080

Reaction notes

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