4-(3-bromopropyl)phenol

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: Under the conditions outlined above for the preparation of 4-[2-(1-methylethyl)aminoethyl]phenol, 4-(3-bromopropyl)phenol was reacted with isopropylamine. The crude product was distilled in a Kugelrohr apparatus (150°; 1 mm) and the distillate was crystallized from ether to give 4-[3-(1-methylethyl)aminopropyl]phenol (97.9% pure by gas chromatography). The crude product was distilled in a Kugelrohr apparatus (150°; 1 mm) the distillate was crystallized from ether

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

Procedure: To 48% hydrobromic acid solution (110 g) was added 4-(3-hydroxypropyl)phenol (25 g) and heated on a steam bath for 3 hours. After cooling, water (500 ml) was added, the oil was extracted with ether, washed with water and then with dilute sodium bicarbonate solution. The etheral extract was dried over potassium carbonate, evaporated and the residue was distilled in a Kugelrohr apparatus giving 29.6 g (84%) of 4-(3-bromopropyl)phenol, bp 180° (2 mm). The product was 92.6% pure by gas chromatography and mass spectrum was compatible with 4-(3-bromopropyl)phenol. heated on a steam bath for 3 hours After cooling the oil was extracted with ether washed with water The etheral extract was dried over potassium carbonate evaporated the residue was distilled in a Kugelrohr apparatus

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

Procedure: To a solution of 1-(4′-hydroxyphenyl)-3-bromopropane 3B (3.56 g) in dichloromethane (11 mL) is added dihydropyran (2.3 mL). The reaction mixture is cooled to 0° C., and three drops of phosphorus oxychloride are added. The reaction mixture is stirred in the ice bath for a further two hours, then gradually allowed to warm to room temperature, where it is allowed to stir overnight. To the reaction mixture is then added potassium carbonate (3 g), and the reaction mixture is stirred an additional hour. The solid is then filtered out, and the solvents and residual DHP is removed in vacuo. to warm to room temperature The solid is then filtered out the solvents and residual DHP is removed in vacuo

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

Procedure: To a solution of 3-(4-hydroxyphenyl)-1-propanol 3A (4.0 g) and tripohenylphosphine (7.96 g) in anhydrous dichloromethane (77 mL), cooled to 0° C., is added, dropwise, a solution of tetrabromomethane (9.59 g) in anhydrous dichloromethane (15.4 mL). The reaction mixture gradually warmed to room temperature and allowed to stir overnight. The solution is then poured into water and extracted with ethyl acetate. The combined organic layers are washed with brine and dried over magnesium sulfate. The solution is concentrated in vacuo. is added extracted with ethyl acetate The combined organic layers are washed with brine dried over magnesium sulfate The solution is concentrated in vacuo

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

Procedure: To a solution of 1-(4′-hydroxyphenyl)-3-bromopropane 3B (3.56 g) in dichloromethane (11 mL) is added dihydropyran (2.3 mL). The reaction mixture is cooled to 0° C., and three drops of phosphorus oxychloride are added. The reaction mixture is stirred in the ice bath for a further two hours, then gradually allowed to warm to room temperature, where it is allowed to stir overnight. To the reaction mixture is then added potassium carbonate (3 g), and the reaction mixture is stirred an additional hour. The solid is then filtered out, and the solvents and residual DHP is removed in vacuo. to warm to room temperature The solid is then filtered out the solvents and residual DHP is removed in vacuo

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

Procedure: A solution of tetrabromomethane (1.125 eq.) in dichloromethane (0.5 ml/mole) was added dropwise to the solution of the commercially available 3-(4-hydroxyphenyl)-1-propanol 1B (1 eq.) and triphenylphosphine (1.125 eq.) in dichloromethane at 0° C. The reaction mixture was stirred at room temperature for 2 days, extracted with dichloromethane, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo. the crude reaction mixture was filtered through silica gel, eluting with 10% ethyl acetate in hexane, to give 3-(4-hydroxyphenyl)-1-bromopropane 2 as a brown oil in 62% yield. extracted with dichloromethane the organic layer was washed with water dried over anhydrous magnesium sulfate The solvent was removed in vacuo the crude reaction mixture was filtered through silica gel eluting with 10% ethyl acetate in hexane

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

Procedure: A solution of tetrabromomethane (1.125 eq.) in dichloromethane (0.5 ml/mole) was added dropwise to the solution of the commercially available 3-(4-hydroxyphenyl)-1-propanol 1B (1 eq.) and triphenylphosphine (1.125 eq.) in dichloromethane at 0° C. The reaction mixture was stirred at room temperature for 2 days, extracted with dichloromethane, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo. the crude reaction mixture was filtered through silica gel, eluting with 10% ethyl acetate in hexane, to give 3-(4-hydroxyphenyl)-1-bromopropane 2 as a brown oil in 62% yield. extracted with dichloromethane the organic layer was washed with water dried over anhydrous magnesium sulfate The solvent was removed in vacuo the crude reaction mixture was filtered through silica gel eluting with 10% ethyl acetate in hexane

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

Procedure: A solution of tetrabromomethane (1.125 eq.) in dichloromethane (0.5 ml/mole) was added dropwise to the solution of the commercially available 3-(4-hydroxyphenyl)-1-propanol 1B (1 eq.) and triphenylphosphine (1.125 eq.) in dichloromethane at 0° C. The reaction mixture was stirred at room temperature for 2 days, extracted with dichloromethane, and the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed in vacuo. the crude reaction mixture was filtered through silica gel, eluting with 10% ethyl acetate in hexane, to give 3-(4-hydroxyphenyl)-1-bromopropane 2 as a brown oil in 62% yield. extracted with dichloromethane the organic layer was washed with water dried over anhydrous magnesium sulfate The solvent was removed in vacuo the crude reaction mixture was filtered through silica gel eluting with 10% ethyl acetate in hexane