2-(4-bromophenoxy)ethyl methanesulfonate

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

Procedure: K2CO3 (29.3 g, 212 mmol) was dissolved in water (162 mL). 1-Propanol (150 mL) was added. A sol. of 2,6-dichloro-para-cresol (25 g, 141 mmol) in 1-propanol (150 mL) was added. Methanesulfonic acid 2-(4-bromo-phenoxy)-ethyl ester (41.6 g, 141 mmol) was added. The mixture was stirred at 85° C. for 6 h. The heating oil bath was removed, and water (330 mL) was added dropwise when the internal temperature had reached 78° C. The beige suspension was allowed to cool to rt. The mixture was filtered, and the precipitate was washed with water. Drying the precipitate under high vacuum at 30° C. for 48 h yielded the title compound (43 g, 81%). LC-MS: tR=1.15 min. The heating oil bath was removed water (330 mL) was added dropwise when the internal temperature had reached 78° C to cool to rt The mixture was filtered the precipitate was washed with water Drying the precipitate under high vacuum at 30° C. for 48 h

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

Procedure: 2-(4-Bromo-phenoxy)-ethanol (125 g, 0.576 mol) was dissolved in CH2Cl2 (650 mL), and the sol. was cooled to 0° C. Et3N (110 mL, 0.864 mol), then mesyl chloride (67.1 mL, 0.864 mol) were dropped at such a speed that the temperature did not raise above 10° C. (about 60 min). The mixture was stirred at 0° C. for 1 h, then at rt overnight. The mixture was diluted with CH2Cl2, and washed with brine (2×). The aq. phase was extracted back with CH2Cl2. The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (174 g, quantitative yield) that was used further without purification. LC-MS: tR=0.92 min. did not raise above 10° C. (about 60 min) at rt overnight washed with brine (2×) The aq. phase was extracted back with CH2Cl2 extracts were dried over MgSO4 filtered the solvents were removed under reduced pressure Drying the residue under high vacuum

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

Procedure: 2-(4-Bromo-phenoxy)-ethanol (125 g, 0.576 mol) was dissolved in CH2Cl2 (650 mL), and the sol. was cooled to 0° C. Et3N (110 mL, 0.864 mol), then mesyl chloride (67.1 mL, 0.864 mol) were dropped at such a speed that the temperature did not raise above 10° C. (about 60 min). The mixture was stirred at 0° C. for 1 h, then at rt overnight. The mixture was diluted with CH2Cl2, and washed with brine (2×). The aq. phase was extracted back with CH2Cl2. The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (174 g, quantitative yield) that was used further without purification. LC-MS: tR=0.92 min. did not raise above 10° C. (about 60 min) at rt overnight washed with brine (2×) The aq. phase was extracted back with CH2Cl2 extracts were dried over MgSO4 filtered the solvents were removed under reduced pressure Drying the residue under high vacuum

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

Procedure: 2-(4-Bromo-phenoxy)-ethanol (125 g, 0.576 mol) was dissolved in CH2Cl2 (650 mL), and the sol. was cooled to 0° C. Et3N (110 mL, 0.864 mol), then mesyl chloride (67.1 mL, 0.864 mol) were dropped at such a speed that the temperature did not raise above 10° C. (about 60 min). The mixture was stirred at 0° C. for 1 h, then at rt overnight. The mixture was diluted with CH2Cl2, and washed with brine (2×). The aq. phase was extracted back with CH2Cl2. The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (174 g, quantitative yield) that was used further without purification. LC-MS: tR=0.92 min. did not raise above 10° C. (about 60 min) at rt overnight washed with brine (2×) The aq. phase was extracted back with CH2Cl2 extracts were dried over MgSO4 filtered the solvents were removed under reduced pressure Drying the residue under high vacuum