4-Bromotoluene → Ethyl 3-(4-methylphenyl)-2-propenoate

HRID 1284858Notes

Reaction equation

HRID 1284858 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[CH:10]=[CH2:11]>[Pd]>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]([CH:11]=[CH:10][C:9]([O:13][CH2:14][CH3:15])=[O:12])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 78054-BromotolueneHCID 8821Ethyl Acrylate

Product 1

HCID 334099Ethyl 3-(4-methylphenyl)-2-propenoateYield 14%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The procedure described in Example 26 is repeated, but using 4.28 g (25 mmols) of 4-bromotoluene and 2.99 ml (27.5 mmols) of ethyl acrylate. After a reaction time of 23 hours at 130° C., 0.67 g (3.5 mmols) of ethyl 4-methylcinnamate is obtained, corresponding to a yield of 14% of theory (conversion figure 1400; Pd content 0.01 mol %).

Sources & evidence

ORD record
ord-daca7fbf1e1f423488e75ef085b7103b
Source dataset
uspto-grants-1986_01
Patent number
US04564479

Reaction notes

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