Water → HCID 67389473, compound

HRID 906604Notes

Reaction equation

HRID 906604 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][C:5]=1[N+]([O-])=O.C([Sn](CCCC)(CCCC)[CH:20]=[CH:21][O:22][CH2:23][CH3:24])CCC.O.CCOC(C)=O>O1CCOCC1>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([C:21]([O:22][CH2:23][CH3:24])=[CH2:20])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2763294(Z)-1-Ethoxy-2-(tributylstannyl)etheneHCID 18350461Methyl 4-bromo-2-nitrobenzoate

Product 1

HCID 67389473HCID 67389473, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-bromo-2-nitro-benzoic acid methyl ester (10 g, 38.5 mmol) tetrakis-(triphenylphosphine)-palladium (4.44 g, 3.84 mmol), and tributyl-(ethoxyvinyl)-tin (21.5 g, 57.8 mmol) in dioxane (125 mL) was heated to 140° C. for 19 h. The mixture was allowed to cool to r.t., and then water and EtOAc were added. The aqueous phase was extracted with EtOAc (3×). The combined organic phases were dried (Na2SO4) and concentrated to dryness. The crude product was purified by flash chromatography (hexanes to EtOAc/hexanes (4:6) to give 4-(1-ethoxy-vinyl)-benzoic acid methyl ester (7.63 g, 30.4 mmol, 79%) as a brown solid. ES-MS: m/z 252 [M+H]+, rt 6.04 min

Workup

  1. extractionThe aqueous phase was extracted with EtOAc (3×)
  2. dry with materialThe combined organic phases were dried (Na2SO4)
  3. concentrationconcentrated to dryness
  4. customThe crude product was purified by flash chromatography (hexanes to EtOAc/hexanes (4:6)

Sources & evidence

ORD record
ord-d786350e41cb40edb7f23bc59084a2f6
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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