2-(2-bromophenoxy)ethanol

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:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium carbonate (23.8 g) and 2-bromophenol (14.9 g) were mixed with dimethylformamide (150 ml). 2-Bromoethanol (12.9 g) was added and the mixture heated to 50° C. for 18 h. The mixture was cooled and added to water (1500 ml). The product was extracted into diethyl ether (×3) and washed twice with dilute sodium hydroxide solution Evaporation gave 2-(2-bromophenoxy)ethanol (17.4 g). The mixture was cooled The product was extracted into diethyl ether (×3) washed twice with dilute sodium hydroxide solution Evaporation

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium carbonate (23.8 g) and 2-bromophenol (14.9 g) were mixed with dimethylformamide (150 ml). 2-Bromoethanol (12.9 g) was added and the mixture heated to 50° C. for 18 h. The mixture was cooled and added to water (1500 ml). The product was extracted into diethyl ether (×3) and washed twice with dilute sodium hydroxide solution Evaporation gave 2-(2-bromophenoxy)ethanol (17.4 g). The mixture was cooled The product was extracted into diethyl ether (×3) washed twice with dilute sodium hydroxide solution Evaporation

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

Procedure: 2-(2-Bromophenoxy)ethanol (17.4 g) was dissolved in dichloromethane (250 ml) and cooled to 0° C. Triethylamine (9.7 g) was added along with tosyl chloride (18.3 g). The mixture was stirred for 2 h, then added to water (500 ml). The organics were washed twice with 2N hydrochloric acid and dried. Separation was achieved using silica chromatography eluting with hexane/ethyl acetate mixtures. This gave 2-(2-bromophenoxy)ethyl tosylate (14.4 g). The organics were washed twice with 2N hydrochloric acid dried Separation eluting with hexane/ethyl acetate mixtures

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a nitrogen atmosphere, 2-bromophenol 5.0 g, 2-bromoethanol 5.42 g, and potassium carbonate 12.0 g were added to N,N-dimethylformamide 30 ml, and the mixture was stirred at 100° C. After about 2.5 hours, the reaction mixture was cooled to room temperature and partitioned by adding water and diethyl ether. The organic layer was washed with water and then with brine, dried over magnesium sulfate anhydride and evaporated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound 5.09 g, 81% was obtained as a colorless oil. the reaction mixture was cooled to room temperature partitioned by adding water and diethyl ether The organic layer was washed with water with brine, dried over magnesium sulfate anhydride evaporated The residue was purified by silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound 5.09 g, 81% was obtained as a colorless oil

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium carbonate (23.8 g) and 2-bromophenol (14.9 g) were mixed with dimethylformamide (150 ml). 2-Bromoethanol (12.9 g) was added and the mixture heated to 50° C. for 18 h. The mixture was cooled and added to water (1500 ml). The product was extracted into diethyl ether (×3) and washed twice with dilute sodium hydroxide solution. Evaporation gave 2-(2-bromophenoxy)ethanol (17.4 g). The mixture was cooled The product was extracted into diethyl ether (×3) washed twice with dilute sodium hydroxide solution Evaporation

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

Procedure: 2-(2-Bromophenoxy)ethanol (17.4 g) was dissolved in dichloromethane (250 ml) and cooled to 0° C. Triethylamine (9.7 g) was added along with tosyl chloride (18.3 g). The mixture was stirred for 2 h, then added to water (500 ml). The organics were washed twice with 2N hydrochloric acid and dried. Separation was achieved using silica chromatography eluting with hexane/ethyl acetate mixtures. This gave 2-(2-bromophenoxy)ethyl tosylate (14.4 g). The organics were washed twice with 2N hydrochloric acid dried Separation eluting with hexane/ethyl acetate mixtures