Diethyl Oxalate → Ethyl 4-(4-bromophenyl)-2,4-dioxobutanoate

HRID 476106Notes

Reaction equation

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

Participants

Reactant 3

HCID 7268Diethyl Oxalate

HCID 7466p-Bromoacetophenone

HCID 5360545Sodium

Product 1

HCID 11066474Ethyl 4-(4-bromophenyl)-2,4-dioxobutanoate

Procedure

The title compound was prepared in the same manner as for intermediate 66 using sodium metal (0.404 g, 17.58 mmol), 1-(4-bromophenyl)ethanone (3.5 g, 17.58 mmol), and diethyl ethanedioate (2.384 mL, 17.58 mmol). The product was collected as 5.1 g (97%). LCMS E-S (M+H)=299.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.22-1.37 (m, 3H), 4.25 (d, J=6.57 Hz, 2H), 7.72 (m, 2H), 7.92 (m, 2H).

Workup

customThe product was collected as 5.1 g (97%)

Sources & evidence

ORD record: ord-7cf7c5efc8eb4a3dba95e910215f6b27
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637509B2

Reaction notes

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