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

HRID 1439056Notes

Reaction equation

HRID 1439056 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° 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 2 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 2 hours more

Sources & evidence

ORD record
ord-1e579c46e04749108de12ec9f6ef53da
Source dataset
uspto-grants-1977_11
Patent number
US04057647

Reaction notes

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