2,4-dichloro-1-ethenylbenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5-bromomethyl-2-propionylamino-benzoic acid methyl ester (172 mg, 0.60 mmol), 2,4-dichloro-1-vinyl-benzene (125 mg, 0.72 mmol), potassium carbonate (100 mg, 0.66 mmol), tri-butyl amine (160 μl, 0.66 mmol) and bis(tri-phenyl-phosphino)palladium (II) di-chloride in DMF (3 ml) was heated to 130° C. After 30 minutes, the reaction mixture was allowed to reach room temperature, acidified with 2 M HCl and the resulting precipitate collected by filtration, washed with water and dried under vacuum to give crude 5-[(E)-2-(2,4-dichloro-phenyl)-vinyl]-2-propionylamino-benzoic acid methyl ester. This was hydrolyzed in ethanol (3 mL) and 1.0 M NaOH (3 mL) overnight and then acidified with 1.0 M HCl. The resulting precipitate was collected by filtration, washed with water and dried under vacuum (136 mg, 62% total yield). 1H-NMR (DMSO-d6) δ 1.14 (t, 3H), 2.43 (q, 2H), 7.32 (d, 1H), 7.37 (d, 1H), 7.44 (dd, 1H), 7.63 (d, 1H), 7.87-7.91 (m, 1H), 8.17 (d, 1H), 8.57 (d, 1H), 11.19 (s, 1H), 13.80 (bs, 1H) to reach room temperature the resulting precipitate collected by filtration washed with water dried under vacuum

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 5-bromomethyl-2-propionylamino-benzoic acid methyl ester (172 mg, 0.60 mmol), 2,4-dichloro-1-vinyl-benzene (125 mg, 0.72 mmol), potassium carbonate (100 mg, 0.66 mmol), tri-butyl amine (160 μl, 0.66 mmol) and bis(tri-phenyl-phosphino)palladium (II) di-chloride in DMF (3 ml) was heated to 130° C. After 30 minutes, the reaction mixture was allowed to reach room temperature, acidified with 2 M HCl and the resulting precipitate collected by filtration, washed with water and dried under vacuum to give crude 5-[(E)-2-(2,4-dichloro-phenyl)-vinyl]-2-propionylamino-benzoic acid methyl ester. This was hydrolyzed in ethanol (3 mL) and 1.0 M NaOH (3 mL) overnight and then acidified with 1.0 M HCl. The resulting precipitate was collected by filtration, washed with water and dried under vacuum (136 mg, 62% total yield). 1H-NMR (DMSO-d6) δ 1.14 (t, 3H), 2.43 (q, 2H), 7.32 (d, 1H), 7.37 (d, 1H), 7.44 (dd, 1H), 7.63 (d, 1H), 7.87-7.91 (m, 1H), 8.17 (d, 1H), 8.57 (d, 1H), 11.19 (s, 1H), 13.80 (bs, 1H) to reach room temperature the resulting precipitate collected by filtration washed with water dried under vacuum