Sulfuric Acid → 3-(2',4'-Difluoro-4-biphenylyl)butane-1,3-diol

HRID 26928

Reaction equation

HRID 26928 reaction equation
[OH:1][CH2:2][CH2:3][C:4](=[O:6])[CH3:5].Br[C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])=[CH:10][CH:9]=1.[Mg].S(=O)(=O)(O)O>CCOCC>[F:21][C:15]1[CH:16]=[C:17]([F:20])[CH:18]=[CH:19][C:14]=1[C:11]1[CH:12]=[CH:13][C:8]([C:4]([OH:6])([CH3:5])[CH2:3][CH2:2][OH:1])=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 1115094-Hydroxy-2-ButanoneHCID 5462224MagnesiumHCID 213226111,1'-Biphenyl, 4'-bromo-2,4-difluoro-

Product 1

HCID 213225623-(2',4'-Difluoro-4-biphenylyl)butane-1,3-diol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

0.44 g. of 1 -hydroxy-3-butanone in 40 ml. of ether is added dropwise, at 20° to stirred Grignard solution obtained from 2.69 g. of 4-bromo-2',4'-difluorobiphenyl and 0.24 g. of magnesium in 100 ml. of ether. The mixture is stirred for two hours more and the resulting alcoholate is decomposed with dilute sulfuric acid. The ether phase is worked up in the customary manner to give 3-(2',4'-difluoro-4-biphenylyl)butane-1,3-diol, m.p. 82°-84°.

Workup

  1. customobtained from 2.69 g
  2. stirringThe mixture is stirred for two hours more

Sources & evidence

ORD record
ord-d3e09d4998144f26af463aa41940b803
Source dataset
uspto-grants-1979_04
Patent number
US04151302

Linked notes

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