Hydrochloric Acid → 4-(3-Chloro-5-fluorophenyl)-5-(3-cyanophenyl)furan-2-carboxylic acid

HRID 2190124Notes

Reaction equation

HRID 2190124 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:22]([O:24]CC)=[O:23])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]#[N:21])[CH:15]=2)[CH:5]=[C:6]([F:8])[CH:7]=1.[OH-].[Li+].O.Cl>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:10]=[C:11]([C:22]([OH:24])=[O:23])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]#[N:21])[CH:15]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 58064795Ethyl 4-(3-chloro-5-fluorophenyl)-5-(3-cyanophenyl)furan-2-carboxylate

Product 1

HCID 580647984-(3-Chloro-5-fluorophenyl)-5-(3-cyanophenyl)furan-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.05 g (2.84 mmol) of the compound from Example 11A are provided in 30 ml of tetrahydrofuran, and 0.68 g (28.4 mmol) of lithium hydroxide and 10 ml of water are added at room temperature. The mixture is stirred at room temperature overnight, a 1N aqueous HCl solution is then added until an acidic pH is established, the mixture is extracted with ethyl acetate and the organic phase is washed with water, dried over sodium sulfate, filtered and concentrated. The crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient). 0.60 g (62% of theory) of the title compound are obtained.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washthe organic phase is washed with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by preparative HPLC (RP18 column; eluent: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-46d158c42a2b48838d1998c0095c319d
Source dataset
uspto-grants-2012_12
Patent number
US08324268B2

Reaction notes

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