Ethyl 4-(3-chloro-4-fluorophenyl)-5-(3-chloro-5-fluorophenyl)thiophene-2-carboxylate → 4-(3-Chloro-4-fluorophenyl)-5-(3-chloro-5-fluorophenyl)thiophene-2-carboxylic acid

HRID 1036993Notes

Reaction equation

HRID 1036993 reaction equation
ClC1C=C(C2SC(C(O)=O)=CC=2C2C=CC=C(C#N)C=2)C=C(F)C=1.[Cl:25][C:26]1[CH:27]=[C:28]([C:33]2[CH:34]=[C:35]([C:46]([O:48]CC)=[O:47])[S:36][C:37]=2[C:38]2[CH:43]=[C:42]([F:44])[CH:41]=[C:40]([Cl:45])[CH:39]=2)[CH:29]=[CH:30][C:31]=1[F:32]>>[Cl:25][C:26]1[CH:27]=[C:28]([C:33]2[CH:34]=[C:35]([C:46]([OH:48])=[O:47])[S:36][C:37]=2[C:38]2[CH:43]=[C:42]([F:44])[CH:41]=[C:40]([Cl:45])[CH:39]=2)[CH:29]=[CH:30][C:31]=1[F:32]

Participants

3

Reactant 2

HCID 58066743Ethyl 4-(3-chloro-4-fluorophenyl)-5-(3-chloro-5-fluorophenyl)thiophene-2-carboxylateHCID 580667575-(3-Chloro-5-fluorophenyl)-4-(3-cyanophenyl)thiophene-2-carboxylic acid

Product 1

HCID 580667454-(3-Chloro-4-fluorophenyl)-5-(3-chloro-5-fluorophenyl)thiophene-2-carboxylic acid

Procedure

The preparation of the title compound takes place in analogy to the synthesis of the compound from Example 19A starting with the compound from Example 12A. The organic phase is concentrated and purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate/ethyl acetate:methanol 1:1 gradient) on silica gel. 0.43 g (100% of theory) of the title compound are obtained.

Workup

  1. concentrationThe organic phase is concentrated
  2. custompurified by flash chromatography (mobile phase: cyclohexane/ethyl acetate/ethyl acetate:methanol 1:1 gradient) on silica gel

Sources & evidence

ORD record
ord-5b488de93749427cbf16c75da2d35efd
Source dataset
uspto-grants-2013_10
Patent number
US08546438B2

Reaction notes

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