Diethyl Oxalate → 6-fluoro-4-oxo-4H-chromene-2-carboxylic acid

Reaction equation

[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[OH:11])=[O:3].CC(C)([O-])C.[K+].[C:18](OCC)(=O)[C:19]([O:21]CC)=[O:20]>>[F:10][C:8]1[CH:7]=[CH:6][C:5]2[O:11][C:18]([C:19]([OH:21])=[O:20])=[CH:1][C:2](=[O:3])[C:4]=2[CH:9]=1

Participants

Reactant 3

HCID 7268Diethyl Oxalate

HCID 959922-Acetyl-4-fluorophenol

HCID 23665647Potassium tert-butoxide

Product 1

HCID 40960466-fluoro-4-oxo-4H-chromene-2-carboxylic acid

Procedure

5-Fluoro-2-hydroxyacetophenone (II) was treated with potassium tertiary butoxide and diethyl oxalate to give 6-fluoro-4-oxo-4H-1-benzopyran-2-carboxylic acid (III) according to Reaction 1 as given below by a known process (JP 2218675).

Sources & evidence

ORD record: ord-7ca5c044dee446d28654d3f122d3973f
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604222B2

Reaction notes

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