3-(4-bromophenyl)prop-2-enoyl chloride

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of sodium azide (NaN3) (2.2 g, 33.8 mmol) in water (7.5 mL) was added dropwise over 5 min to a stirred solution of 4-bromocinnamoyl chloride (22.2 mmol) in acetone (22 mL) at −10° C. The heterogeneous mixture was stirred at 0° C. for 1 h and diluted with water (25 mL). The precipitate was collected by filtration and dried in vacuo over phosphorus pentoxide (P2O5) to give 4-bromocinnamoyl azide (5.22 g, 20.7 mmol) as a golden-coloured solid. The precipitate was collected by filtration dried in vacuo over phosphorus pentoxide (P2O5)

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

Procedure: A solution of 4-bromocinnamic acid (5.03 g, 22.2 mmol) in thionyl chloride (SOCl2) (15 mL) was stirred at 23° C. for 16 h, and then heated at reflux for a further 2 h. The solvents were evaporated in vacuo and the residue azeotroped with toluene (×3) to yield 4-bromocinnamoyl chloride as an orange-brown solid in quantitative yield. heated at reflux for a further 2 h The solvents were evaporated in vacuo the residue azeotroped with toluene (×3)

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

Procedure: 7-Bromo-1,4-dichloroisoquinoline ##STR100## A solution of 4-bromocinnamic acid (5.03 g, 22.2 mmol) in SOCl2 (15 mL) was stirred at 23° C. for 16 h, and then heated at reflux for a further 2 h. The solvents were evaporated in vacuo and the residue azeotroped with PhMe (×3) to yield 4-bromocinnamoyl chloride (22 mmol) as an orange-brown solid. heated at reflux for a further 2 h The solvents were evaporated in vacuo the residue azeotroped with PhMe (×3)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of NaN3 (2.2 g, 33.8 mmol) in water (7.5 mL) was added dropwise over 5 min to a stirred solution of 4-bromocinnamoyl chloride (22 mmol) in acetone (22 mL) at -10° C. The heterogeneous mixture was stirred at 0° C. for 1 h and diluted with water (25 mL). The precipitate was collected by filtration and dried in vacuo over P2O5 to give 4-bromocinnamoyl azide (5.22 g, 20.7 mmol) as a golden-coloured solid. The precipitate was collected by filtration dried in vacuo over P2O5

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

Procedure: 7-Bromo-1,4-dichloroisoquinoline ##STR100## A solution of 4-bromocinnamic acid (5.03 g, 22.2 mmol) in SOCl2 (15 mL) was stirred at 23° C. for 16 h, and then heated at reflux for a further 2 h. The solvents were evaporated in vacuo and the residue azeotroped with PhMe (×3) to yield 4-bromocinnamoyl chloride (22 mmol) as an orange-brown solid. heated at reflux for a further 2 h The solvents were evaporated in vacuo the residue azeotroped with PhMe (×3)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium azide (67 g, 1 mol) was suspended in a mixture of water and acetone (300 mL, 1:1). The mixture was cooled to 0° C., a solution of compound 3 (126.9 g, 0.52 mol) in dry acetone (400 mL) was added at 5° C. The resulting mixture was stirred at 0-5° C. for 4 h and then poured into water (1.5 L). The precipitate was filtered off, washed with water, dried. Additional drying in vacuo over P2O5 gave 4 (130.3 g, 100%) The precipitate was filtered off washed with water dried Additional drying in vacuo over P2O5

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

Procedure: A solution of compound 2 (113.8 g, 0.5 mol) in thionyl chloride was refluxed for 1.5 h. Then the mixture was concentrated in vacuo and the crude product 3 was obtained (126.9 g, 93%). Then the mixture was concentrated in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of sodium azide (NaN3) (2.2 g, 33.8 mmol) in water (7.5 mL) was added dropwise over 5 min to a stirred solution of 4-bromocinnamoyl chloride (22.2 mmol) in acetone (22 mL) at −10° C. The heterogeneous mixture was stirred at 0° C. for 1 h and diluted with water (25 mL). The precipitate was collected by filtration and dried in vacuo over phosphorus pentoxide (P2O5) to give 4-bromocinnamoyl azide (5.22 g, 20.7 mmol) as a golden-coloured solid. The precipitate was collected by filtration dried in vacuo over phosphorus pentoxide (P2O5)

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

Procedure: A solution of 4-bromocinnamic acid (5.03 g, 22.2 mmol) in thionyl chloride (SOCl2) (15 mL) was stirred at 23° C. for 16 h, and then heated at reflux for a further 2 h. The solvents were evaporated in vacuo and the residue azeotroped with toluene (×3) to yield 4-bromocinnamoyl chloride as an orange-brown solid in quantitative yield. heated at reflux for a further 2 h The solvents were evaporated in vacuo the residue azeotroped with toluene (×3)