3,5-dibromobenzoyl chloride

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

Procedure: By the general method for the synthesis of 2-(2,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole in Example 3, the reaction of 3,5-dibromobenzoyl chloride (20.13 g, 0.06747 mole) with 4-octoxybenzoyl hydrazide (17 g, 0.06747 mole) gave the intermediate 3,5-dibromo-N′-[4-(octyloxy)benzoyl]benzohydrazide (12.87 g, 36% yield). Cyclocondensation of the intermediate 3,5-dibromo-N′-[4-(oxtyloxy)benzoyl]-benzohydrazide (12.17 g) with POCl3 (63 mL) gave 2-(3,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole (6.12 g, 52% yield).

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

Procedure: By the general method for the synthesis of 2-(2,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole in Example 3, the reaction of 3,5-dibromobenzoyl chloride (20.13 g, 0.06747 mole) with 4-octoxybenzoyl hydrazide (17 g, 0.06747 mole) gave the intermediate 3,5-dibromo-N′-[4-(octyloxy)benzoyl]benzohydrazide (12.87 g, 36% yield). Cyclocondensation of the intermediate 3,5-dibromo-N′-[4-(oxtyloxy)benzoyl]-benzohydrazide (12.17 g) with POCl3 (63 mL) gave 2-(3,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole (6.12 g, 52% yield).

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

Procedure: By the general method for the synthesis of 2-(2,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole in Example 1, the reaction of 3,5-dibromobenzoyl chloride (20.13 g, 0.06747 mole) with 4-octyloxybenzoic acid hydrazide (17 g, 0.06747 mole) gave the intermediate 3,5-dibromo-N′-[4-(octyloxy)benzoyl]benzohydrazide (12.87 g, 36% yield). Cyclocondensation of the intermediate 3,5-dibromo-N′-[4-(octyloxy)benzoyl]-benzohydrazide (12.17 g) with POCl3 (63 mL) gave the required 2-(3,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole (6.12 g, 52% yield).

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

Procedure: By the general method for the synthesis of 2-(2,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole in Example 1, the reaction of 3,5-dibromobenzoyl chloride (20.13 g, 0.06747 mole) with 4-octyloxybenzoic acid hydrazide (17 g, 0.06747 mole) gave the intermediate 3,5-dibromo-N′-[4-(octyloxy)benzoyl]benzohydrazide (12.87 g, 36% yield). Cyclocondensation of the intermediate 3,5-dibromo-N′-[4-(octyloxy)benzoyl]-benzohydrazide (12.17 g) with POCl3 (63 mL) gave the required 2-(3,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole (6.12 g, 52% yield).

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

Procedure: By the general method for the synthesis of 2-(2,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole (1) in Example 3, the reaction of 3,5-dibromobenzoyl chloride (20.13 g, 0.06747 mole) with 4-octoxybenzoyl hydrazide (17 g, 0.06747 mole) gave the intermediate 3,5-dibromo-N′-[4-(octyloxy)benzoyl]benzohydrazide (12.87 g, 36% yield). Cyclocondensation of the intermediate 3,5-dibromo-N′-[4-(octyloxy)benzoyl]-benzohydrazide (12.17 g) with POCl3 (63 mL) gave the required 2-(3,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole (5) (6.12 g, 52% yield).

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

Procedure: By the general method for the synthesis of 2-(2,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole (1) in Example 3, the reaction of 3,5-dibromobenzoyl chloride (20.13 g, 0.06747 mole) with 4-octoxybenzoyl hydrazide (17 g, 0.06747 mole) gave the intermediate 3,5-dibromo-N′-[4-(octyloxy)benzoyl]benzohydrazide (12.87 g, 36% yield). Cyclocondensation of the intermediate 3,5-dibromo-N′-[4-(octyloxy)benzoyl]-benzohydrazide (12.17 g) with POCl3 (63 mL) gave the required 2-(3,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole (5) (6.12 g, 52% yield).

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

Procedure: 2.98 g of 3,5-dibromobenzoyl chloride and 3.58 g of 4-biphenylcarbonitrile were dissolved in 40 mL of chloroform. The obtained solution was cooled to 0° C., and 2.99 g of antimony pentachloride was added dropwise to the cooled solution. The obtained mixed liquid was stirred at room temperature for 10 minutes, and then, heated under reflux for 14 hours. The obtained reaction mixture was cooled to room temperature, and then distilled under a reduced pressure to remove chloroform to give 4,6-bis(4-biphenylyl)-2-(3,5-dibromophenyl)-1,3,5-oxadiazin-1-ium=hexachloroantimonate as a red solid. The obtained mixed liquid heated under reflux for 14 hours The obtained reaction mixture was cooled to room temperature distilled under a reduced pressure to remove chloroform

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

Procedure: 2.98 g of 3,5-dibromobenzoyl chloride and 3.58 g of 4-biphenylcarbonitrile were dissolved in 40 mL of chloroform. The obtained solution was cooled to 0° C., and 2.99 g of antimony pentachloride was added dropwise to the cooled solution. The obtained mixed liquid was stirred at room temperature for 10 minutes, and then, heated under reflux for 14 hours. The obtained reaction mixture was cooled to room temperature, and then distilled under a reduced pressure to remove chloroform to give 4,6-bis(4-biphenylyl)-2-(3,5-dibromophenyl)-1,3,5-oxadiazin-1-ium=hexachloroantimonate as a red solid. The obtained mixed liquid heated under reflux for 14 hours The obtained reaction mixture was cooled to room temperature distilled under a reduced pressure to remove chloroform

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

Procedure: By the general method for the synthesis of 2-(2,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole (1) in Example 3, the reaction of 3,5-dibromobenzoyl chloride (20.13 g, 0.06747 mole) with 4-octoxybenzoyl hydrazide (17 g, 0.06747 mole) gave the intermediate 3,5-dibromo-N′-[4-(octyloxy)benzoyl]benzohydrazide (12.87 g, 36% yield). Cyclocondensation of the intermediate 3,5-dibromo-N′-[4-(octyloxy)benzoyl]-benzohydrazide (12.17 g) with POCl3 (63 mL) gave the required 2-(3,5-dibromophenyl)-5-[4-(octyloxy)phenyl]-1,3,4-oxadiazole (5) (6.12 g, 52% yield).

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

Procedure: In a flask equipped with a reflux condenser, 84 g (0.3 mole) of 3,5-dibromobenzoic acid and 68 g (0.33 mole) of phosphorus pentachloride were reacted under reflux for one hour. After removal of phosphorus oxychloride under reduced pressure by means of an aspirator, the reaction product was subjected to vacuum distillation under 8 mm Hg to obtain 63 g of 3,5-dibromobenzoic acid chloride, melting at 125° to 130° C., in the form of a colorless transparent liquid (yield: 70%). In a flask equipped with a reflux condenser under reflux for one hour After removal of phosphorus oxychloride under reduced pressure by means of an aspirator the reaction product was subjected to vacuum distillation under 8 mm Hg

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

Procedure: In a stream of argon, a 300 ml three-necked flask equipped with a reflux condenser was charged with 3,5-dibromobenzoyl chloride (10.5 g) and 5-chlorobiphenyl-3-carbonitrile (15.0 g), and then chlorobenzene (100 mL) was added to the content. The thus-obtained solution was cooled to 0° C., and antimony pentachloride (10.5 g) was dropwise added thereto. The resultant mixture was stirred at room temperature for 20 minutes and then refluxed at 100° C. for 2.5 hours. The thus-obtained red-colored solution was cooled to −20° C., and an aqueous 28% ammonia solution (50 mL) was added to obtain a milky white liquid suspension. The suspension was stirred at room temperature for 3 hours, and then, gradually heated to 140° C. in an oil bath to distill away the organic solvent (80 mL) and water (28 mL). Chlorobenzene (100 mL×3) was added to the solution, and then the solution was filtered at 130° C. The filtrate was left to stand at room temperature, and then methanol (300 mL) was added thereto. The thus-obtained solid precipitate was collected by filtration, and washed with methanol twice (50 mL×2) and dried. Thus, 2.21 g of 4,6-bis(5-chlorobiphenyl-3-yl)-2-(3,5-dibromophenyl)-1,3,5-triazine was obtained as a white powder (yield: 9%). In a stream of argon, a 300 ml three-necked flask equipped with a reflux condenser refluxed at 100° C. for 2.5 hours The thus-obtained red-colored solution was cooled to −20° C. to obtain a milky white liquid suspension gradually heated to 140° C. in an oil bath to distill away the organic solvent (80 mL) and water (28 mL) Chlorobenzene (100 mL×3) was added to the solution the solution was filtered at 130° C The filtrate was left to stand at room temperature methanol (300 mL) was added The thus-obtained solid precipitate was collected by filtration washed with methanol twice (50 mL×2) dried

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

Procedure: In a flask equipped with a reflux condenser, 84 g (0.3 mole) of 3,5-dibromobenzoic acid and 68 g (0.33 mole) of phosphorus pentachloride were reacted under reflux for one hour. After removal of phosphorus oxychloride under reduced pressure by means of an aspirator, the reaction product was subjected to vacuum distillation under 8 mm Hg to obtain 63 g of 3,5-dibromobenzoic acid chloride, melting at 125° to 130° C.; in the form of a colorless transparent liquid (yield: 70%). In a flask equipped with a reflux condenser under reflux for one hour After removal of phosphorus oxychloride under reduced pressure by means of an aspirator the reaction product was subjected to vacuum distillation under 8 mm Hg