1,8-Dibromooctane → 8-(4-Methylphenyl)octylbromide

Reaction equation

[Cl-].[Li+].Br[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][Br:12].[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([Mg]Br)=[CH:16][CH:15]=1>C1COCC1>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][Br:12])=[CH:16][CH:15]=1

Participants

Procedure

Lithium chloride (0.15 g, 3.5 mmol) and cupric chloride (0.3 g, 2.2 mmol) were added to THF (100 ml) and stirred for 1 hour 30 minutes. 1,8-Dibromooctane (37 g, 137 mmol) was then added. While keeping the temperature between 0° C. and 5° C., 4-methylphenyl magnesium bromide in THF (prepared from magnesium (2.3 g, 95 mmol) and 4-methylphenyl bromide (15.4 g, 90 mmol) in THF (150 ml)) was added over 1 hour, allowing the temperature to reach room temperature overnight. The reaction mixture was poured over concentrated hydrochloric acid/ice mixture and the product was extracted into ether. The ether was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulphate and evaporated to give an oil, which was distilled under vacuum to give 8-(4-methylphenyl)octylbromide as an oil, bp 128° at 0.2mm.