Diethyl Oxalate → ethyl 6-bromo-8-nitro-4-oxo-4H-1-benzopyran-2-carboxylate

Reaction equation

[CH3:1][C:2]([C:4]1[C:9]([OH:10])=[C:8]([N+:11]([O-:13])=[O:12])[CH:7]=[C:6]([Br:14])[CH:5]=1)=[O:3].[C:15](OCC)(=O)[C:16]([O:18][CH2:19][CH3:20])=[O:17]>>[Br:14][C:6]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[C:9]2[O:10][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:1][C:2](=[O:3])[C:4]=2[CH:5]=1

Participants

Reactant 2

HCID 7268Diethyl Oxalate

HCID 6890715'-Bromo-2'-hydroxy-3'-nitroacetophenone

Product 1

HCID 19606344ethyl 6-bromo-8-nitro-4-oxo-4H-1-benzopyran-2-carboxylateYield 77%

Procedure

Following the process described in example 1 (point A), starting from 5-bromo-2-hydroxy-3-nitroacetophenone and diethyl oxalate, the title compound was prepared, which was purified by crystallization in tetrahydrofuran:ethanol mixtures (77% yield).

Workup

customwhich was purified by crystallization in tetrahydrofuran

Sources & evidence

ORD record: ord-229865d3952146b6b1534cdfe4980eeb
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05990142

Reaction notes

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