4-[4-(Bromomethyl)phenyl]sulfonylmorpholine

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

Procedure: The aforementioned compound 1, (500 mg, 1.56 mmol) and triethyl phosphite (1.07 mL, 6.24 mmol) was mixed and heated to 100° C. for 1 hr. The reaction mixture was subjected to N2 flow over weekend to remove the excess ethyl phosphite. The resulting yellow oil was purified on a 12 g silica gel column to yield a colorless oil (420 mg, 71% yield). 1H NMR (CD2Cl2) δ ppm: 7.72 (d, J=8.4 Hz, 2H), 7.54 (dd, J1=8.4 Hz, J2=2.4 Hz, 2H), 4.1-4.0 (m, 4H), 3.77-3.72 (m, 4H), 3.25 (d, J=22.4 Hz, 2H), 3.02-2.96 (m, 4H), 1.27 (t, J=7.2 Hz, 6H). to remove the excess ethyl phosphite The resulting yellow oil was purified on a 12 g silica gel column

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

Procedure: The aforementioned compound 1, (500 mg, 1.56 mmol) and triethyl phosphite (1.07 mL, 6.24 mmol) was mixed and heated to 100° C. for 1 hr. The reaction mixture was subjected to N2 flow over weekend to remove the excess ethyl phosphite. The resulting yellow oil was purified on a 12 g silica gel column to yield a colorless oil (420 mg, 71% yield). 1H NMR (CD2Cl2) δ ppm: 7.72 (d, J=8.4 Hz, 2H), 7.54 (dd, J1=8.4 Hz, J2=2.4 Hz, 2H), 4.1-4.0 (m, 4H), 3.77-3.72 (m, 4H), 3.25 (d, J=22.4 Hz, 2H), 3.02-2.96 (m, 4H), 1.27 (t, J=7.2 Hz, 6H). to remove the excess ethyl phosphite The resulting yellow oil was purified on a 12 g silica gel column

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

Procedure: To a solution of 4-bromomethylbenzenesulfonyl chloride (1.62 g, 6.01 mmol) in anhydrous diethyl ether (10 mL) at −10° C. was added a solution of morpholine (0.52 mL, 5.94 mmol) and triethylamine (0.92 mL, 6.6 mmol) in anhydrous diethyl ether (10 mL). The resulting mixture was allowed to warm up to room temperature over 1 hr, and continue stirring at r.t. overnight. The reaction mixture was then diluted with water, extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with water, brine, dried over Na2SO4, and filtered. Solvents were removed to yield an orange oil, which was purified on a 40 g silica gel column to give a white solid (1.34 g, 71% yield). 1H NMR (CD2Cl2) δ ppm: 7.75 (d, J=8.4 Hz, 2H), 7.63 (d, J=8.4 Hz, 2H), 4.58 (s, 2H), 3.77-3.73 (m, 2H), 3.03-2.98 (m, 2H). MS (ESI+): 320 (M+H)+. extracted with ethyl acetate (2×30 mL) The combined organic layers were washed with water, brine dried over Na2SO4 filtered Solvents were removed to yield an orange oil, which was purified on a 40 g silica gel column

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

Procedure: To a solution of 4-bromomethylbenzenesulfonyl chloride (1.62 g, 6.01 mmol) in anhydrous diethyl ether (10 mL) at −10° C. was added a solution of morpholine (0.52 mL, 5.94 mmol) and triethylamine (0.92 mL, 6.6 mmol) in anhydrous diethyl ether (10 mL). The resulting mixture was allowed to warm up to room temperature over 1 hr, and continue stirring at r.t. overnight. The reaction mixture was then diluted with water, extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with water, brine, dried over Na2SO4, and filtered. Solvents were removed to yield an orange oil, which was purified on a 40 g silica gel column to give a white solid (1.34 g, 71% yield). 1H NMR (CD2Cl2) δ ppm: 7.75 (d, J=8.4 Hz, 2H), 7.63 (d, J=8.4 Hz, 2H), 4.58 (s, 2H), 3.77-3.73 (m, 2H), 3.03-2.98 (m, 2H). MS (ESI+): 320 (M+H)+. extracted with ethyl acetate (2×30 mL) The combined organic layers were washed with water, brine dried over Na2SO4 filtered Solvents were removed to yield an orange oil, which was purified on a 40 g silica gel column

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

Procedure: The aforementioned compound 1, (500 mg, 1.56 mmol) and triethyl phosphite (1.07 mL, 6.24 mmol) was mixed and heated to 100° C. for 1 hr. The reaction mixture was subjected to N2 flow over weekend to remove the excess ethyl phosphite. The resulting yellow oil was purified on a 12 g silica gel column to yield a colorless oil (420 mg, 71% yield). 1H NMR (CD2Cl2) δ ppm: 7.72 (d, J=8.4 Hz, 2H), 7.54 (dd, J1=8.4 Hz, J2=2.4 Hz, 2H), 4.1-4.0 (m, 4H), 3.77-3.72 (m, 4H), 3.25 (d, J=22.4 Hz, 2H), 3.02-2.96 (m, 4H), 1.27 (t, J=7.2 Hz, 6H). to remove the excess ethyl phosphite The resulting yellow oil was purified on a 12 g silica gel column

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

Procedure: To a solution of 4-bromomethylbenzenesulfonyl chloride (1.62 g, 6.01 mmol) in anhydrous diethyl ether (10 mL) at −10° C. was added a solution of morpholine (0.52 mL, 5.94 mmol) and triethylamine (0.92 mL, 6.6 mmol) in anhydrous diethyl ether (10 mL). The resulting mixture was allowed to warm up to room temperature over 1 hr, and continue stirring at r.t. overnight. The reaction mixture was then diluted with water, extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with water, brine, dried over Na2SO4, and filtered. Solvents were removed to yield an orange oil, which was purified on a 40 g silica gel column to give a white solid (1.34 g, 71% yield). 1H NMR (CD2Cl2) δ ppm: 7.75 (d, J=8.4 Hz, 2H), 7.63 (d, J=8.4 Hz, 2H), 4.58 (s, 2H), 3.77-3.73 (m, 2H), 3.03-2.98 (m, 2H). MS (ESI+): 320 (M+H)+. extracted with ethyl acetate (2×30 mL) The combined organic layers were washed with water, brine dried over Na2SO4 filtered Solvents were removed to yield an orange oil, which was purified on a 40 g silica gel column

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir: