Heck Coupling

General Procedure:

Bromo-aromatic ring (1 equiv.), methyl acrylate (5 equiv.), TEA (1.5 equiv.), catalyst Pd(OAc)2 (0.1 equiv.), and P(o-Tolyl)3 (0.1 equiv.) were mixed in acetonitrile (depends on the scale). The mixture was degassed and heated to reflux for 5 hours under nitrogen atmosphere. The resulting mixture was filtered with celite and the filtrate was concentrated. The resultant residue was purified by silica gel column to give rise to the desired compound.

Note:

• The reaction conditions tolerate a wide range of functional groups on the olefin (Esters, ethers, carboxylic acids, nitriles, phenols, dienes are well tolerated on the olefin component. However, allylic alcohols tend to undergo rearrangement)

• Heck Coupling is stereospecific. Both the migratory insertion and the hydride elimination proceed with syn stereochemistry.

• Aryl chlorides are not good substrates, as they tend to react slowly, resulting in lower yields.

• Substrates with beta-hydrogen atoms undergoes beta-elimination, leading to olefin formation

• When the olefin substrate is more substituted, the reaction proceeds slower

For more details on reactions and reagents, 
refer to the tab "Reaction, Reagents and Mechanism"

Typical Procedure:

• High temperature Heck coupling of (2-bromo-5-methoxy-3-methylphenyl)-acetonitrile with ethyl acrylate (ChemSpider) — Open access

For more details on large-scale reactions and OPRD procedures, 
refer to the tab "Scale-up & Green Chem"

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