1-bromo-4-octylbenzene

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

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 50 ml of THF (tetrahydrofuran) was added to 2.91 g (0.12 mol) of metallic magnesium, and the mixture was stirred. 100 ml of a solution of 26.89 g (0.1 mol) of p-octylbromobenzene in THF was added dropwise thereto, and the mixture was heated. After the initiation of the reaction was confirmed, the mixture was refluxed for one hr. The mixture was cooled to −78° C., 12.46 g (0.12 mol) of trimethylboric acid was added dropwise thereto, and the mixture was stirred for 30 min. The temperature was returned to room temperature, followed by stirring for additional one hr. Dilute hydrochloric acid was added thereto, and the mixture was stirred for one hr. The aqueous layer was extracted with ether, and the oil layer was washed with water and then with an aqueous sodium hydrogencarbonate. The oil layer was then dried over sodium sulfate, the solvent was removed by distillation, and the resultant crude product was purified by chromatography on silica gel to give p-octylphenylboric acid. the mixture was heated the mixture was refluxed for one hr the mixture was stirred for 30 min was returned to room temperature by stirring for additional one hr the mixture was stirred for one hr The aqueous layer was extracted with ether the oil layer was washed with water The oil layer was then dried over sodium sulfate the solvent was removed by distillation the resultant crude product was purified by chromatography on silica gel

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 50 ml of THF (tetrahydrofuran) was added to 2.91 g (0.12 mol) of metallic magnesium, and the mixture was stirred. 100 ml of a solution of 26.89 g (0.1 mol) of p-octylbromobenzene in THF was added dropwise thereto, and the mixture was heated. After the initiation of the reaction was confirmed, the mixture was refluxed for one hr. The mixture was cooled to −78° C., 12.46 g (0.12 mol) of trimethylboric acid was added dropwise thereto, and the mixture was stirred for 30 min. The temperature was returned to room temperature, followed by stirring for additional one hr. Dilute hydrochloric acid was added thereto, and the mixture was stirred for one hr. The aqueous layer was extracted with ether, and the oil layer was washed with water and then with an aqueous sodium hydrogencarbonate. The oil layer was then dried over sodium sulfate, the solvent was removed by distillation, and the resultant crude product was purified by chromatography on silica gel to give p-octylphenylboric acid. the mixture was heated the mixture was refluxed for one hr the mixture was stirred for 30 min was returned to room temperature by stirring for additional one hr the mixture was stirred for one hr The aqueous layer was extracted with ether the oil layer was washed with water The oil layer was then dried over sodium sulfate the solvent was removed by distillation the resultant crude product was purified by chromatography on silica gel

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

Procedure: A Grignard reagent was prepared from magnesium (2.3 g) and 4-octyl-1-bromobenzene (25 g) dissolved in dry tetrahydrofuran (hereinafter abbreviated to THF, 200 ml). To this Grignard reagent were added 2,5-dibromopyridine (23 g) and tetrakistriphenylphosphin paradiun (0) complex (hereinafter abbreviated to Pd(TPP)4, 0.57 g). The reaction mixture was heated to keep refluxing for about 2 hours. After cooling the mixture, organic matter was extracted from the mixture with ether, followed by sequential washing the extract with aqueous ammonium chloride and distilled water to separate an organic layer which was dried over MgSO4. Filtering off the desiccant and distilling off the solvent from the organic layer, the layer gave a residue which was purified by silica gel column chromatography to give 5-bromo-2-(4-octylphenyl)pyridine (35 g). The reaction mixture was heated to keep refluxing for about 2 hours After cooling the mixture, organic matter was extracted from the mixture with ether by sequential washing the extract with aqueous ammonium chloride distilled water to separate an organic layer which was dried over MgSO4 Filtering off the desiccant and distilling off the solvent from the organic layer the layer gave a residue which was purified by silica gel column chromatography

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

Procedure: To a suspension of magnesium (1.477 g, 60.8 mmol) in THF (56 mL) was added 1-bromo-4-octylbenzene (15.00 g, 55.7 mmol). After stirring for about 6 h the reaction mixture was added with filtering to a solution of 3-ethoxycyclohex-2-enone (7.10 g, 50.6 mmol) in THF (28.0 mL) at 0° C. Following the addition the reaction mixture was allowed to warm to room temperature. After 1 h 1N HCl was added until a pH of 1 was obtained. The reaction mixture was diluted with Et2O and the organic layer was separated, washed with NaHCO3, and brine, dried with (Na2SO4, filtered and concentrated in vacuo. The crude product was purified by chromatography on silica gel (EtOAc/Hep) to provide 3-(4-octylphenyl)cyclohex-2-enone (9.5 g, 33.4 mmol, 65.9% yield) as a colorless oil. was added the addition the reaction mixture was obtained the organic layer was separated washed with NaHCO3, and brine dried with (Na2SO4 filtered concentrated in vacuo The crude product was purified by chromatography on silica gel (EtOAc/Hep)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 50 ml of THF (tetrahydrofuran) was added to 2.91 g (0.12 mol) of metallic magnesium, and the mixture was stirred. 100 ml of a solution of 26.89 g (0.1 mol) of p-octylbromobenzene in THF was added dropwise thereto, and the mixture was heated. After the initiation of the reaction was confirmed, the mixture was refluxed for one hr. The mixture was cooled to −78° C., 12.46 g (0.12 mol) of trimethylboric acid was added dropwise thereto, and the mixture was stirred for 30 min. The temperature was returned to room temperature, followed by stirring for additional one hr. Dilute hydrochloric acid was added thereto, and the mixture was stirred for one hr. The aqueous layer was extracted with ether, and the oil layer was washed with water and then with an aqueous sodium hydrogencarbonate. The oil layer was then dried over sodium sulfate, the solvent was removed by distillation, and the resultant crude product was purified by chromatography on silica gel to give p-octylphenylboric acid. the mixture was heated the mixture was refluxed for one hr the mixture was stirred for 30 min was returned to room temperature by stirring for additional one hr the mixture was stirred for one hr The aqueous layer was extracted with ether the oil layer was washed with water The oil layer was then dried over sodium sulfate the solvent was removed by distillation the resultant crude product was purified by chromatography on silica gel