2,4-Difluoro-1,1'-biphenyl → 1-(2',4'-Difluoro-4-biphenylyl)-3-methoxypropan-1-one

HRID 26925

Reaction equation

HRID 26925 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:15][O:16][CH2:17][CH2:18][C:19](Cl)=[O:20]>CCOCC>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C:19](=[O:20])[CH2:18][CH2:17][O:16][CH3:15])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 1699742,4-Difluoro-1,1'-biphenylHCID 27597283-Methoxypropanoyl chloride

Product 1

HCID 213226091-(2',4'-Difluoro-4-biphenylyl)-3-methoxypropan-1-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2.62 g. of 1-(2',4'-difluoro-4-biphenylyl)-3-hydroxypropan-1-one, obtained by acylating 2,4-difluorobiphenyl with 3-methoxypropionyl chloride to give 1-(2',4'-difluoro-4-biphenylyl)-3-methoxypropan-1-one and subsequently effecting ether scission, in 20 ml. of THF is added dropwise, at 20° to stirred Grignard solution prepared from 3 g. of methyl iodide and 0.5 g. of magnesium in 100 ml. of ether. The mixture is stirred for 4 hours more and the resulting alcoholate is decomposed with water and dilute sulfuric acid. The reaction mixture is worked up in the customary manner to give 3-(2',4'-difluoro-4-biphenylyl)butane-1,3-diol, m.p. 82°-84°.

Sources & evidence

ORD record
ord-390123433cac401c96a642aa04ae275e
Source dataset
uspto-grants-1979_04
Patent number
US04151302

Linked notes

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