Acetate → Flurbiprofen

HRID 903109Notes

Reaction equation

HRID 903109 reaction equation
[Tl].C([O-])(=O)C.[F:6][C:7]1[CH:12]=[C:11]([CH:13]([CH3:18])[C:14]([O:16]C)=[O:15])[CH:10]=[CH:9][C:8]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(O)(=O)C.CCCCCC>[F:6][C:7]1[CH:12]=[C:11]([CH:13]([CH3:18])[C:14]([OH:16])=[O:15])[CH:10]=[CH:9][C:8]=1[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 175AcetateHCID 4127Flurbiprofen Methyl EsterHCID 5359464Thallium

Product 1

HCID 3394Flurbiprofen

Reagents, catalysts & solvents 1

HCID 22590778Acetic Acid HexaneSolvent

Procedure

Following the procedure of Example 2, the enol ether of the formula ##STR2## is reacted with thallium (lll) acetate in an aqueous acetic acid/hexane mixture at 25° to 50° C. until methyl 2-(2-fluoro-4-biphenylyl)propionate is formed. This ester is isolated from the reaction mixture and hydrolyzed to 2-(2-fluoro-4-biphenylyl)propionic acid (generic name, flurbiprofen) by the described procedure.

Workup

  1. customis formed

Sources & evidence

ORD record
ord-e69669eaae284500911b8cdc59cc1fe4
Source dataset
uspto-grants-1980_10
Patent number
US04226790

Reaction notes

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