Bromobenzene → Ethyl 3-phenylprop-2-enoate

HRID 1194569Notes

Reaction equation

HRID 1194569 reaction equation
[I-].I[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.BrC1C=CC=CC=1.[C:16]([O:20][CH2:21][CH3:22])(=[O:19])[CH:17]=[CH2:18]>ClC1C=CC=CC=1>[C:16]([O:20][CH2:21][CH3:22])(=[O:19])[CH:17]=[CH:18][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 7961BromobenzeneHCID 8821Ethyl AcrylateHCID 11575IodobenzeneHCID 30165Iodide Ion

Product 1

HCID 7649Ethyl 3-phenylprop-2-enoate

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

More specifically, we have found that chlorobenzene reacts with ethyl acrylate to form ethyl cinnamate in relatively high yield by reacting the chlorobenzene with iodide and/or bromide ion to form a mixture of chlorobenzene, iodobenzene and/or bromobenzene, then reacting the mixture with ethyl acrylate in the presence of a catalyst to form ethyl cinnamate.

Workup

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Sources & evidence

ORD record
ord-6f72a208a7344acea8fc457e2fec1a80
Source dataset
uspto-grants-1989_03
Patent number
US04814489

Reaction notes

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