Tetraethyltin → Methyl 2-ethyl-5-nitrobenzoate

HRID 47441

Reaction equation

HRID 47441 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1Br.[Cl-].[Li+].[CH2:17]([Sn](CC)(CC)CC)[CH3:18]>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 11704TetraethyltinHCID 245494Methyl 2-Bromo-5-nitrobenzoateHCID 433294Lithium Chloride

Product 1

HCID 54220219Methyl 2-ethyl-5-nitrobenzoateYield 55.9%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-Bromo-5-nitrobenzoic acid methyl ester (1.0 g), lithium chloride (0.49 g), tetraethyltin (0.96 g) and bis(triphenylphosphine)-palladium(II)chloride (0.1 g) were combined in dimethylformamide (20 ml) and heated at 100° C. for 8 h. Solvent was removed at reduced pressure and the residue column chromatographed (silica gel, dichloromethane/petroleum ether 30:70) to give the title compound (0.45 g). 1H NMR (CDCl3) δ: 1.28 (3H, t, J=7.4 Hz), 3.10 (2H, q, J=7.4Hz), 3.96 (3H, s), 7.47 (1H, d, J=8.5 Hz), 8.27 (1H, dd, J=2.5, 8.5 Hz), 8.73 (1H, d, J=2.5 Hz)

Workup

  1. customSolvent was removed at reduced pressure
  2. customthe residue column chromatographed (silica gel, dichloromethane/petroleum ether 30:70)

Sources & evidence

ORD record
ord-04238d49458a47fa88198787870212fd
Source dataset
uspto-grants-2004_03
Patent number
US06699879B1

Linked notes

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