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

HRID 1036992Notes

Reaction equation

HRID 1036992 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[S:13][C:12]([C:14]([O:16]CC)=[O:15])=[CH:11][C:10]=2[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=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[S:13][C:12]([C:14]([OH:16])=[O:15])=[CH:11][C:10]=2[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 58066751Ethyl 5-(3-chloro-5-fluorophenyl)-4-(3-cyanophenyl)thiophene-2-carboxylate

Product 1

HCID 580667575-(3-Chloro-5-fluorophenyl)-4-(3-cyanophenyl)thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

130 mg (0.34 mmol) of the compound from Example 11A are provided in 6.1 ml of tetrahydrofuran, and 80.7 mg (3.37 mmol) of lithium hydroxide and 2.0 ml of water are added at room temperature. The mixture is stirred at room temperature overnight, a 1N aqueous HCl solution is subsequently added until an acidic pH is obtained, the mixture is extracted with ethyl acetate and the extract is dried over sodium sulfate, filtered and concentrated. 119 mg (89% of theory) of the title compound are obtained.

Workup

  1. customis obtained
  2. extractionthe mixture is extracted with ethyl acetate
  3. dry with materialthe extract is dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b19f6e7d2d65412492d0693e23f889c6
Source dataset
uspto-grants-2013_10
Patent number
US08546438B2

Reaction notes

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