Sodium 4-fluorophenolate → 3-(4'-Fluoro-4-biphenylyl)-3-methyl-pyrazolidin-5-one

HRID 1576425Notes

Reaction equation

HRID 1576425 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:14])[CH2:12][C:11](=[O:13])[NH:10][NH:9]2)=[CH:4][CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([O-])=[CH:18][CH:17]=1.[Na+]>CN(C=O)C>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[CH:7]=[CH:6][C:5]([C:8]3([CH3:14])[CH2:12][C:11](=[O:13])[NH:10][NH:9]3)=[CH:4][CH:3]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 23682312Sodium 4-fluorophenolateHCID 545522463-p-Iodophenyl-3-methyl-pyrazolidin-5-one

Product 1

HCID 215126753-(4'-Fluoro-4-biphenylyl)-3-methyl-pyrazolidin-5-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 30.2 g of 3-p-iodophenyl-3-methyl-pyrazolidin-5-one (obtainable from p-iodoacetophenone via 3-hydroxy-3-p-iodophenyl-butyric acid ethyl ester and 3-p-iodophenyl-2-butenoic acid ethyl ester) and 13.4 g of sodium p-fluorophenolate in 200 ml of DMF is warmed for 8 hours at 130°. Working up in the usual manner gives 3-(4'-fluoro-4-biphenylyl)-3-methyl-pyrazolidin-5-one, m.p. 194°-196°.

Sources & evidence

ORD record
ord-f36d31dd663245f6933b6dd72719ef1a
Source dataset
uspto-grants-1976_09
Patent number
US03980795

Reaction notes

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