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

HRID 1439043Notes

Reaction equation

HRID 1439043 reaction equation
Br[CH2:2][C:3]([OH:5])=[O:4].[Br-].C([Zn+])C=C.C(Br)C=C.[C:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[F:31])=[CH:20][CH:19]=1)(=[O:17])[CH3:16].[Na+].[Br-].Cl>C1COCC1.[Zn].[Hg](I)I>[F:31][C:25]1[CH:26]=[C:27]([F:30])[CH:28]=[CH:29][C:24]=1[C:21]1[CH:22]=[CH:23][C:18]([C:15]([OH:17])([CH3:16])[CH2:2][C:3]([OH:5])=[O:4])=[CH:19][CH:20]=1

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 7841Allyl bromideHCID 1045421-(2',4'-Difluoro(1,1'-biphenyl)-4-yl)ethan-1-oneHCID 253881Sodium BromideHCID 178455868HCID 178455868, compound

Product 1

HCID 213225833-(2',4'-Difluoro-4-biphenylyl)-3-hydroxybutyric acid

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst3×HCID 244857774-29-0CatalystHCID 8028TetrahydrofuranSolvent4×

Procedure

A solution of 12.9 g. of bromoacetic acid in 50 ml. of THF is added slowly dropwise at 10°-15° to a solution of 19 g. of allyl-zinc bromide in 200 ml. of THF, prepared by reacting allyl bromide with zinc filings in THF. A solution of 23.2 g. of 4-acetyl-2',4'-difluorobiphenyl in 100 ml. of THF, 6.5 g. of zinc filings, 100 mg. of HgI2 and 10.3 g. of NaBr are added to the reaction mixture, which contains an intermediate of the formula BrCH2 -COOZnBr, and heated under reflux until all the zinc has dissolved. After the alcholate formed has been decomposed with dilute hydrochloric acid, the mixture is worked up in the customary manner to give 3-(2',4'-difluoro-4-biphenylyl)-3-hydroxybutyric acid, m.p. 121°-123°.

Workup

  1. temperatureheated
  2. dissolutionhas dissolved
  3. customAfter the alcholate formed

Sources & evidence

ORD record
ord-9e120e94955749679e8839c788553997
Source dataset
uspto-grants-1977_11
Patent number
US04057647

Reaction notes

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