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

HRID 26937

Reaction equation

HRID 26937 reaction equation
C([O:3][C:4](OCC)(OCC)[O:5]CC)C.[F:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[C:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH3:32])[CH2:29][Mg]Br)=[CH:24][CH:23]=1.BrCC(C1C=CC(C2C=CC(F)=CC=2F)=CC=1)C.Cl>C1COCC1>[F:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[C:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH3:32])[CH2:29][C:4]([OH:5])=[O:3])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 66213Tetraethyl orthocarbonateHCID 536914404'-(1-Bromopropan-2-yl)-2,4-difluoro-1,1'-biphenylHCID 178455852HCID 178455852, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 g. of orthocarbonic acid tetraethyl ester are added to a solution of 2-(2',4'-difluoro-4-biphenylyl)-1-propylmagnesium bromide, prepared from 3.11 g. of 4-(1-bromo-2-propyl)-2',4'-difluorobiphenyl, in 40 ml. of THF and the mixture is stirred for 4 hours at 25°. Excess dilute hydrochloric acid is added slowly. The mixture is heated under reflux for 24 hours, allowed to cool and worked up in the customary manner to give 3-(2',4'-difluoro-4-biphenylyl)butyric acid, m.p. 109°-110°.

Workup

  1. customprepared from 3.11 g
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for 24 hours
  4. temperatureto cool

Sources & evidence

ORD record
ord-ef8912ff8fa343f4841630136022f423
Source dataset
uspto-grants-1979_04
Patent number
US04151302

Linked notes

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