8-bromooctanoyl chloride

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

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

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

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

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

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

Procedure: Aluminum chloride (1.74 g) was added to a solution of 8-bromooctanoyl chloride (3 g) in benzene (20 ml), and the mixture was stirred at room temperature for 1.5 hr. Ice water and conc. hydrochloric acid were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 1.36 g of 8-bromo-1-phenyl-1-octanone. the mixture was extracted with ethyl acetate The organic layer was washed with water and brine dried the solvent was evaporated under reduced pressure The obtained residue was purified by silica gel column chromatography

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

Procedure: 8-Bromooctanoic acid (200 g) was added slowly to thionyl chloride (325 ml). The mixture was stirred at 60° for 1 hour. Excess thionyl chloride distilled off in vacuo. The dark oily residue was distilled to give 8-bromooctanoyl chloride as colorless oil, b.p. 112°-114°/0.1-0.3 mm Hg, (202.38, 93%). Excess thionyl chloride distilled off in vacuo The dark oily residue was distilled

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

Procedure: Compound 2 (n=4) (3.2 g, 15.7 mmol) was treated with 8-bromooctanoyl chloride (4.55 g, 18.8 mmol) in CH2Cl2 and 1N NaOH following the procedure used for (3). Silica gel column chromatography with 2:1 hexane/EtOAc afforded 3.8 g (59%) of [I] as an oil: NMR δ 1.17-2.00 (m, 14 H), 2.23-2.50 (m, 4 H), 3.37 (t, 2 H, J=6), 3.63 (t, 2 H, J=6), 4.77 (s, 2 H), 7.33 (s, 5 H). Anal. (C20H29BrN2O2) C, H, N.

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

Procedure: 1-(4-Chlorophenyl)-1-methylethylamine hydrochloride (4.0 g) was reacted with 8-bromooctanoyl chloride (4.7 g) in dichloromethane (50 ml) containing triethylamine (8.1 ml), in a similar manner to Example 52b, to give 8-bromo-N-[1-(4-chlorophenyl)-1-methylethyl]octanamide which was used directly in part c).

Conditions: temp:95.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 8-bromooctanoic acid (26.4 g), thionyl chloride (40 ml) and acetonitrile (40 ml) was heated at 95° C. for 3 hours. The solvent was removed by distillation under vacuum and the residue purified by azeotropic distillation, using acetonitrile, to give 8-bromooctanoyl chloride. The solvent was removed by distillation under vacuum the residue purified by azeotropic distillation

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

Procedure: Aluminum chloride (1.74 g) was added to a solution of 8-bromooctanoyl chloride (3 g) in benzene (20 ml), and the mixture was stirred at room temperature for 1.5 hr. Ice water and conc. hydrochloric acid were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 1.36 g of 8-bromo-1-phenyl-1-octanone. the mixture was extracted with ethyl acetate The organic layer was washed with water and brine dried the solvent was evaporated under reduced pressure The obtained residue was purified by silica gel column chromatography

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

Procedure: 8-Bromooctanoic acid (200 g) was added slowly to thionyl chloride (325 ml). The mixture was stirred at 60° for 1 hour. Excess thionyl chloride distilled off in vacuo. The dark oily residue was distilled to give 8-bromooctanoyl chloride as colorless oil, b.p. 112°-114°/0.1-0.3 mm Hg, (202.38, 93%). Excess thionyl chloride distilled off in vacuo The dark oily residue was distilled