tert-butyl N-[3-(4-chlorophenyl)-3-hydroxypropyl]carbamate

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

Procedure: Triphenylphosphine (1.61 g, 6.12 mmol) was added to a solution of tert-butyl 3-(4-chlorophenyl)-3-hydroxypropylcarbamate (1.40 g, 4.90 mmol) in DCM (30 mL) at about 0° C. NBS (1.05 g, 5.88 mmol) was added portionwise. After 2 h, the reaction mixture was loaded to a short silica gel pad and eluted with EtOAc:hexanes (1:5) to give tert-butyl 3-bromo-3-(4-chlorophenyl)propylcarbamate (0.79 g, 46%) as an oil, which solidified on standing. 1H NMR (CDCl3, 400 MHz) δ 7.35 (m, 4H), 4.96 (m, 1H), 4.63 (br s, 1H), 3.28 (m, 2H), 3.21 (m, 1H), 2.37 (m, 2H), 1.44 (s, 9H). eluted with EtOAc:hexanes (1:5)

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

Procedure: Triphenylphosphine (1.61 g, 6.12 mmol) was added to a solution of tert-butyl 3-(4-chlorophenyl)-3-hydroxypropylcarbamate (1.40 g, 4.90 mmol) in DCM (30 mL) at about 0° C. NBS (1.05 g, 5.88 mmol) was added portionwise. After 2 h, the reaction mixture was loaded to a short silica gel pad and eluted with EtOAc:hexanes (1:5) to give tert-butyl 3-bromo-3-(4-chlorophenyl)propylcarbamate (0.79 g, 46%) as an oil, which solidified on standing. 1H NMR (CDCl3, 400 MHz) δ 7.35 (m, 4H), 4.96 (m, 1H), 4.63 (br s, 1H), 3.28 (m, 2H), 3.21 (m, 1H), 2.37 (m, 2H), 1.44 (s, 9H). eluted with EtOAc:hexanes (1:5)

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

Procedure: Triphenylphosphine (1.61 g, 6.12 mmol) was added to a solution of tert-butyl 3-(4-chlorophenyl)-3-hydroxypropylcarbamate (1.40 g, 4.90 mmol) in DCM (30 mL) at about 0° C. NBS (1.05 g, 5.88 mmol) was added portionwise. After 2 h, the reaction mixture was loaded to a short silica gel pad and eluted with EtOAc:hexanes (1:5) to give tert-butyl 3-bromo-3-(4-chlorophenyl)propylcarbamate (0.79 g, 46%) as an oil, which solidified on standing. 1H NMR (CDCl3, 400 MHz) δ 7.35 (m, 4H), 4.96 (m, 1H), 4.63 (br s, 1H), 3.28 (m, 2H), 3.21 (m, 1H), 2.37 (m, 2H), 1.44 (s, 9H). eluted with EtOAc:hexanes (1:5)

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

Procedure: Triphenylphosphine (1.61 g, 6.12 mmol) was added to a solution of tert-butyl 3-(4-chlorophenyl)-3-hydroxypropylcarbamate (1.40 g, 4.90 mmol) in DCM (30 mL) at about 0° C. NBS (1.05 g, 5.88 mmol) was added portionwise. After 2 h, the reaction mixture was loaded to a short silica gel pad and eluted with EtOAc:hexanes (1:5) to give tert-butyl 3-bromo-3-(4-chlorophenyl)propylcarbamate (0.79 g, 46%) as an oil, which solidified on standing. 1H NMR (CDCl3, 400 MHz) δ 7.35 (m, 4H), 4.96 (m, 1H), 4.63 (br s, 1H), 3.28 (m, 2H), 3.21 (m, 1H), 2.37 (m, 2H), 1.44 (s, 9H). eluted with EtOAc:hexanes (1:5)