1-bromo-2-[(E)-2-phenylethenyl]benzene

反応条件: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of the Grignard reagent prepared from E-1-phenyl-2-(2-bromophenyl)ethylene (8.56 g) and magnesium (0.96 g) in dry tetrahydrofuran (20 ml) was added dropwise over 30 minutes to a stirred solution of dimethyl oxalate (7.76 g) in dry tetrahydrofuran (70 ml) cooled to −15° C. The resulting mixture was stirred at about −15° C. for 30 minutes, then at room temperature for 1 hour, then poured into dilute hydrochloric acid and extracted with ether. The extracts were washed with water, dried and concentrated to give the crude product as a yellow oil (17.22 g). Purification by column chromatography using dichloromethane and petrol (1:1) as eluant then evaporative distillation (0.07 torr, oven temperature 170° C.) gave E-methyl 2-(2′-phenylethenyl)phenylglyoxalate (2.01 g, 23% yield) as a yellow oil, pure by GC, 1H nmr (CDCl3): delta 3.78 (3H, s), 6.88 (centre of 2 doublets, each 1H, J 16 Hz) p.p.m. at room temperature for 1 hour extracted with ether The extracts were washed with water dried concentrated to give the crude product as a yellow oil (17.22 g) Purification by column chromatography distillation (0.07 torr, oven temperature 170° C.)

反応条件: temp:170.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A stirred mixture of 1-(2-bromophenyl)-2-phenylethan-1-ol (15.50 g) and orthophosphoric acid (150 ml) was heated at 170° C. for 1 hour and then poured into iced water and extracted with ether. The extracts were washed with water, dried and concentrated to give the crude product as an orange oil (14.29 g). Evaporative distillation (0.3 torr; oven temperature 140° C.) gave E-1-phenyl-2(2-bromophenyl)ethylene (12.53 g, 86% yield) as a pale yellow oil with a purity of 97% by GC. extracted with ether The extracts were washed with water dried concentrated to give the crude product as an orange oil (14.29 g) Evaporative distillation (0.3 torr; oven temperature 140° C.)

反応条件: temp:170.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A stirring mixture of 1-(2-bromophenyl)-2-phenyl-ethan-1-ol (15.50 g) and orthophosphoric acid (150 ml) was heated at 170° C. for 1 hour and then poured into iced water and extracted with ether. The extracts were washed with water, dried and concentrated to give the crude product as an orange oil (14.29 g). Evaporative distillation (0.3 torr; oven temperature 140° C.) gave E-1-phenyl-2(2bromophenyl)ethylene (12.53 g), 86% yield) as a pale yellow oil with a purity of 97% by GC. extracted with ether The extracts were washed with water dried concentrated to give the crude product as an orange oil (14.29 g) Evaporative distillation (0.3 torr; oven temperature 140° C.)

反応条件: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of the Grignard reagent prepared from E-1-phenyl-2-(2-bromophenyl)ethylene (8.56 g) and magnesium (0.96 g) in dry tetrahydrofuran (20 ml) was added dropwise over 30 minutes to a stirred solution of dimethyl oxalate (7.76 g) in dry tetrahydrofuran (70 ml) cooled to −15° C. The resulting mixture was stirred at about −15° C. for 30 minutes, then at room temperature for 1 hour, then poured into dilute hydrochloric acid and extracted with ether. The extracts were washed with water, dried and concentrated to give the crude product as a yellow oil (17.22 g). Purification by column chromatography using dichloromethane and petrol (1:1) as eluant then evaporative distillation (0.07 torr, oven temperature 170° C.) gave E-methyl 2-(2′-phenylethenyl)phenylglyoxalate (2.01 g, 23% yield) as a yellow oil, pure by GC, 1H nmr (CDCl3): delta 3.78 (3H, s), 6.88 (centre of 2 doublets, each 1H, J 16 Hz) p.p.m. at room temperature for 1 hour extracted with ether The extracts were washed with water dried concentrated to give the crude product as a yellow oil (17.22 g) Purification by column chromatography distillation (0.07 torr, oven temperature 170° C.)

反応条件: temp:170.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A stirred mixture of 1-(2-bromophenyl)-2-phenylethan-1-ol (15.50 g) and orthophosphoric acid (150 ml) was heated at 170° C. for 1 hour and then poured into iced water and extracted with ether. The extracts were washed with water, dried and concentrated to give the crude product as an orange oil (14.29 g). Evaporative distillation (0.3 torr; oven temperature 140° C.) gave E-1-phenyl-2(2-bromophenyl)ethylene (12.53 g, 86% yield) as a pale yellow oil with a purity of 97% by GC. extracted with ether The extracts were washed with water dried concentrated to give the crude product as an orange oil (14.29 g) Evaporative distillation (0.3 torr; oven temperature 140° C.)

反応条件: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of the Grignard reagent prepared from E-1-phenyl-2-(2 -bromophenyl)ethylene (8.56 g) and magnesium (0.96 g) in dry tetrahydrofuran (20 ml) was added dropwise over 30 minutes to a stirred solution of dimethyl oxalate (7.76 g) in dry tetrahydrofuran (70 ml) cooled to -15° C. The resulting mixture was stirred at about -15° C. for 30 minutes, then at room temperature for 1 hour, then poured into dilute hydrochloric acid and extracted with ether. The extracts were washed with water, dried and concentrated to give the crude product as a pale yellow oil (17.22 g). Purification by column chromatography using dichloromethane and petrol (1:1) as eluant then evaporative distillation (0.07 torr, oven temperature 170° C.) gave E-methyl 2-(2'-phenylethenyl)phenylglyoxalate (2.01 g, 23% yield) as a yellow oil, pure by GC, 1H nmr (CDCl3) : delta 3.78 (3H, s), 6.88 (centre of 2 doublets, each 1 H, J 16Hz) p.p.m. at room temperature for 1 hour extracted with ether The extracts were washed with water dried concentrated to give the crude product as a pale yellow oil (17.22 g) Purification by column chromatography distillation (0.07 torr, oven temperature 170° C.)

反応条件: temp:170.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A stirred mixture of 1-(2-bromophenyl)-2-phenylethan-1-ol (15.50 g) and orthophosphoric acid (150 ml) was heated at 170° C. for 1 hour and then poured into iced water and extracted with ether. The extracts were washed with water, dried and concentrated to give the crude product as an orange oil (14.29 g). Evaporative distillation (0.3 torr; oven temperature 140° C.) gave E-1-phenyl-2-(2-bromophenyl)ethylene (12.53 g, 86% yield) as a pale yellow oil with a purity of 97% by GC. extracted with ether The extracts were washed with water dried concentrated to give the crude product as an orange oil (14.29 g) Evaporative distillation (0.3 torr; oven temperature 140° C.)

反応条件: temp:170.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A stirring mixture of 1-(2-bromophenyl)-2-phenyl-ethan-1-ol (15.50 g) and orthophosphoric acid (150 ml) was heated at 170° C. for 1 hour and then poured into iced water and extracted with ether. The extracts were washed with water, dried and concentrated to give the crude product as an orange oil (14.29 g). Evaporative distillation (0.3 torr; oven temperature 140° C.) gave E-1-phenyl-2(2bromophenyl)ethylene (12.53 g), 86% yield) as a pale yellow oil with a purity of 97% by GC. extracted with ether The extracts were washed with water dried concentrated to give the crude product as an orange oil (14.29 g) Evaporative distillation (0.3 torr; oven temperature 140° C.)

反応条件: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A solution of the Grignard reagent prepared from E-1-phenyl-2-(2-bromophenyl)ethylene (8.56 g) and magnesium (0.96 g) in dry tetrahydrofuran (20 ml) was added dropwise over 30 minutes to a stirred solution of dimethyl oxalate (7.76 g) in dry tetrahydrofuran (70 ml) cooled to −15° C. The resulting mixture was stirred at about −15° C. for 30 minutes, then at room temperature for 1 hour, then poured into dilute hydrochloric acid and extracted with ether. The extracts were washed with water, dried and concentrated to give the crude product as a yellow oil (17.22 g). Purification by column chromatography using dichloromethane and petrol (1:1) as eluant then evaporative distillation (0.07 torr, oven temperature 170° C.) gave E-methyl 2-(2′-phenylethenyl)phenylglyoxalate (2.01 g, 23% yield) as a yellow oil, pure by GC, 1H nmr (CDCl3): delta 3.78 (3H, s), 6.88 (centre of 2 doublets, each 1H, J 16 Hz) p.p.m. at room temperature for 1 hour extracted with ether The extracts were washed with water dried concentrated to give the crude product as a yellow oil (17.22 g) Purification by column chromatography distillation (0.07 torr, oven temperature 170° C.)

反応条件: temp:170.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A stirred mixture of 1-(2-bromophenyl)-2-phenylethan-1-ol (15.50 g) and orthophosphoric acid (150 ml) was heated at 170° C. for 1 hour and then poured into iced water and extracted with ether. The extracts were washed with water, dried and concentrated to give the crude product as an orange oil (14.29 g). Evaporative distillation (0.3 torr; oven temperature 140° C.) gave E-1-phenyl-2(2-bromophenyl)ethylene (12.53 g, 86% yield) as a pale yellow oil with a purity of 97% by GC. extracted with ether The extracts were washed with water dried concentrated to give the crude product as an orange oil (14.29 g) Evaporative distillation (0.3 torr; oven temperature 140° C.)