Ethyl Acrylate → Ethyl 3-(4-nitrophenyl)-2-propenoate

HRID 1284860Notes

Reaction equation

HRID 1284860 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=[CH2:13]>[Pd]>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([CH:13]=[CH:12][C:11]([O:15][CH2:16][CH3:17])=[O:14])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 8821Ethyl AcrylateHCID 114661-Bromo-4-nitrobenzene

Product 1

HCID 95370Ethyl 3-(4-nitrophenyl)-2-propenoateYield 88%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The procedure described in Example 26 is repeated, but using 5.05 g (25 mmols) of 4-bromonitrobenzene and 2.99 ml (27.5 mmols) of ethyl acrylate. After a reaction time of 3 hours at 130° C., 4.86 g (22.0 mmols) of ethyl 4-nitrocinnamate are obtained, corresponding to a yield of 88% of theory (conversion figure 8800; Pd content 0.01 mol %).

Sources & evidence

ORD record
ord-12e9710d8fdc4b15a000d589b0f735ed
Source dataset
uspto-grants-1986_01
Patent number
US04564479

Reaction notes

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