1-chloro-4-(3-methoxypropyl)benzene

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: A mixture of 3-(4-chlorophenyl)propyl methyl ether (8.6 g, 46.5 mmol), N-bromosuccinimide (NBS; 9.43 g, 52.9 mmol), and a catalyst amount of 2,2′-azobisisobutyronitrile in ethylene dichloride (236 ml) was heated at 65° to 70° C. for three hours. The cooled reaction mixture was washed successively with water, saturated aqueous sodium bicarbonate and water, dried over anhydrous sodium sulfate and concentrated in vacuo to afford crude title compound (13.3 g) which was used without further purification. The cooled reaction mixture was washed successively with water, saturated aqueous sodium bicarbonate and water dried over anhydrous sodium sulfate concentrated in vacuo

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

Procedure: To a stirred solution of 3-(4-chlorophenyl)propanol (9.61 g, 54.17 mmol) and methyl iodide (7.0 ml, 112 mmol) in dry tetrahydrofuran (85 ml) under nitrogen was added 60% sodium hydride (2.83 g, 70.8 mmol) in portions. The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was treated with ice/water (150 ml), extracted with methylene chloride (3×250 ml), and the combined organic extracts were washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo. Chromatography of the residual yellow oil on silica gel eluting with hexane afforded the title compound as a yellow oil (8.69 g, 86% from 3-(4-chlorophenyl)propionic acid) which was characterized by NMR spectral analysis. extracted with methylene chloride (3×250 ml) the combined organic extracts were washed with water dried over anhydrous sodium sulfate concentrated in vacuo