Ethyl Acetoacetate → 3-(2',4'-Difluoro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester

HRID 26927Notes

Reaction equation

HRID 26927 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[F:15])=[CH:4][CH:3]=1.[Mg].[C:17]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:18][C:19]([CH3:21])=[O:20].[NH4+].[Cl-]>CCOCC>[CH2:24]([O:23][C:17](=[O:22])[CH2:18][C:19]([C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[F:15])=[CH:4][CH:3]=1)([OH:20])[CH3:21])[CH3:25]

Participants

6

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 213226111,1'-Biphenyl, 4'-bromo-2,4-difluoro-

Product 1

HCID 538342513-(2',4'-Difluoro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2',4'-difluoro-4-biphenylylmagnesium bromide, obtained from 2.69 g. of 4-bromo-2',4'-difluorobiphenyl and 0.24 g. of magnesium in 100 ml. of ether, is added dropwise at 20° to a stirred solution of 1.3 g. of ethyl acetoacetate in 40 ml. of ether. The mixture is stirred for 2 hours more and the resulting alcoholate is decomposed with ice and saturated NH4Cl solution. The ether phase is dried and evaporated to give 3-(2',4'-difluoro-4-biphenylyl)-3-hydroxybutyric acid ethyl ester, m.p. 96°-97°.

Workup

  1. dry with materialThe ether phase is dried
  2. customevaporated

Sources & evidence

ORD record
ord-1f7605c9d79d453f862d4707344f834e
Source dataset
uspto-grants-1979_04
Patent number
US04151302

Reaction notes

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