5-bromopentylbenzene

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:

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: Phosphorus tribromide (4.7 ml, 49.8 mmol) was added dropwise to a solution of 5-phenylpentan-1-ol (3 ml, 17.8 mmol) in dioxane (70 ml). The reaction mixture was stirred for 2 hours at room temperature. Another portion of phosphorus tribromide (4.7 m. 49.8 mmol) was added. The reaction mixture was stirred for 16 h at room temprature. It was cooled to 0° C. Water (60 ml) was added dropwise. The reaction mixture was diluted with ethyl acetate (100 ml). The phases were separated. The aqueous phase was extracted with ethyl acetate (2×100 ml). The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) and dried over magnesium sulfate. The solvent was removed in vacuo. The crude product was purified by flash chromatography on silica (50 g), using ethyl acetate/heptane (1:10) as eluent, to give 1.35 g of 1-bromo-5-phenylpentane. The reaction mixture was stirred for 16 h at room temprature It was cooled to 0° C The phases were separated The aqueous phase was extracted with ethyl acetate (2×100 ml) The combined organic layers were washed with a saturated aqueous solution of sodium hydrogencarbonate (200 ml) dried over magnesium sulfate The solvent was removed in vacuo The crude product was purified by flash chromatography on silica (50 g)

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

Procedure: 2-Acetamido-1,3-bis(tert-butyldimethylsilyloxy)-2-(2-(4-formylphenyl)ethyl)propane (3.0 g) and 1-bromo-5-phenylpentane (4.1 g) were reacted and treated in the same manner as in Working example 1(6) to give the title compound (2.7 g) as a pale yellow oily substance.

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Compound 3-6 (380 mg) was dissolved in N,N-dimethylformamide (10 ml), potassium carbonate (277 mg) and 5-phenylpentylbromide (281 mg) were added, and the mixture was stirred at 80° C. for 6 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the object product (560 mg) as a colorless oil. the mixture was extracted with ethyl acetate washed with water and saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure

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

Procedure: At 0° C., 50 g (0.304 mol) of 5-phenylpentan-1-ol are added to a solution of 416.7 ml (1.83 mol) of 48% strength hydrobromic acid, and the mixture is stirred at 0° C. for 30 min. The reaction solution is then stirred at 100° C. for 12 hours. After the reaction has gone to completion, the mixture is cooled to room temperature, and 200 ml of ethyl acetate are added. After extraction, the organic phase is separated off, washed with saturated sodium bicarbonate and dried over sodium sulfate. After filtration, the filtrate is evaporated to dryness. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane). This gives 59.4 g (0.26 mol, 86% of theory) of a colorless liquid. The reaction solution is then stirred at 100° C. for 12 hours the mixture is cooled to room temperature After extraction the organic phase is separated off washed with saturated sodium bicarbonate dried over sodium sulfate After filtration the filtrate is evaporated to dryness