Diethyl (ethoxymethylene)malonate → HCID 86628010, compound

HRID 1486936Notes

Reaction equation

HRID 1486936 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[F:9].C(O[CH:13]=[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])C>CCO>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:4][C:3]=1[F:9]

Participants

4

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 8218484-Bromo-3-fluoroaniline

Product 1

HCID 86628010HCID 86628010, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-bromo-3-fluoroaniline (56.6 g, 297.87 mmol) and 1,3-diethyl 2-(ethoxymethylidene)propanedioate (72.45 g, 335.06 mmol) in EtOH (560 mL) was stirred at 80° C. for 4 h. The reaction mixture was allowed to cool, the solids collected by filtration and dried in an oven to afford the desired material (90 g, 84%) as an off-white solid which was used without further purification. NMR Spectrum: 1H NMR (400 MHz, DMSO-d6) δ 1.26 (6H, q), 4.14 (2H, q), 4.22 (2H, q), 7.18-7.25 (1H, m), 7.57 (1H, dd), 7.64-7.7 (1H, m), 8.33 (1H, d), 10.62 (1H, d). Mass Spectrum: m/z (ES+)[M+H]+=360.

Workup

  1. temperatureto cool
  2. filtrationthe solids collected by filtration
  3. customdried in an oven

Sources & evidence

ORD record
ord-cbe0ef10e0b04e598fcef528b5c542e4
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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