p-Bromochlorobenzene → 2-Propenoic acid, 3-(4-chlorophenyl)-, ethyl ester

HRID 1284859Notes

Reaction equation

HRID 1284859 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.[C:9]([O:13][CH2:14][CH3:15])(=[O:12])[CH:10]=[CH2:11]>[Pd]>[Cl: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 7806p-BromochlorobenzeneHCID 8821Ethyl Acrylate

Product 1

HCID 2014712-Propenoic acid, 3-(4-chlorophenyl)-, ethyl esterYield 72%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

The procedure described in Example 26 is repeated, but using 4.79 g (25 mmols) of 4-bromochlorobenzene and 2.99 ml (27.5 mmols) of ethyl acrylate. After a reaction time of 8 hours at 130° C., 3.79 g (18.0 mmols) of ethyl 4-chlorocinnamate are obtained, corresponding to a yield of 72% of theory (conversion figure 7200; Pd content 0.01 mol %).

Sources & evidence

ORD record
ord-9d2e236336e64d17a9d2b3adbf160d6d
Source dataset
uspto-grants-1986_01
Patent number
US04564479

Reaction notes

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