Hydrochloric Acid → 3-(2',4'-Difluoro-4-biphenylyl)butyric acid

HRID 26930Notes

Reaction equation

HRID 26930 reaction equation
BrC([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])=[CH:6][CH:5]=1)C.[C:18]([O:24]CC)(=[O:23])[CH2:19][C:20]([CH3:22])=O.[OH-].[K+].Cl>O>[F:17][C:11]1[CH:12]=[C:13]([F:16])[CH:14]=[CH:15][C:10]=1[C:7]1[CH:8]=[CH:9][C:4]([CH:20]([CH3:22])[CH2:19][C:18]([OH:24])=[O:23])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8868Ethyl AcetoacetateHCID 14797Potassium HydroxideHCID 213226214'-(1-Bromoethyl)-2,4-difluoro-1,1'-biphenyl

Product 1

HCID 213225403-(2',4'-Difluoro-4-biphenylyl)butyric acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1 g. of 2-[1-(2',4'-difluoro-4-biphenylyl)ethyl]-butan-3-one acid ethyl ester, obtained by reacting 4-(1-bromoethyl)-2',4'-difluorobiphenyl with ethyl acetoacetate, and 15 ml. of 50% KOH are stirred for 45 minutes at 90° under N2. The mixture is cooled, diluted with water and brought to pH 10 with HCl. The reaction mixture is washed with ether and worked up in the customary manner to give 3-(2',4'-difluoro-4-biphenylyl)butyric acid, m.p. 109°-110°.

Workup

  1. temperatureThe mixture is cooled
  2. washThe reaction mixture is washed with ether

Sources & evidence

ORD record
ord-4cd57f63a59d4a3eb147ee771db36661
Source dataset
uspto-grants-1979_04
Patent number
US04151302

Reaction notes

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