1-(2-bromo-3-methylanilino)-2-methylpropan-2-ol

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

Procedure: To a solution of potassium tert-butoxide (472 mg, 4.21 mmol) in THF (4 mL) was added a solution of 1-(2-bromo-3-methylphenylamino)-2-methylpropan-2-ol (724 mg, 2.80 mmol) in THF (10 mL), followed by ethyl 2-chloroacetate (0.45 mL, 4.21 mmol). After 1 h at RT an additional 1 eq of potassium t-butoxide (472 mg, 4.21 mmol) and ethyl 2-chloroacetate (0.450 mL, 4.21 mmol) were added. After 6 h water was added, followed by EtOAc. The organic phase was separated, dried over MgSO4 and the solvent was removed under reduced pressure. The remaining residue was purified by flash chromatography (30-80% EtOAc/hexanes). 4-(2-Bromo-3-methylphenyl)-6,6-dimethylmorpholin-3-one was isolated as a light-yellow solid. The organic phase was separated dried over MgSO4 the solvent was removed under reduced pressure The remaining residue was purified by flash chromatography (30-80% EtOAc/hexanes)

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

Procedure: To a solution of lithium perchlorate (2.13 g, 20 mmol) in diethyl ether (4 mL) was added 1,2-epoxy-2-methylpropane (0.195 mL, 2.2 mmol), followed by 2-bromo-3-methylaniline (0.250 mL, 2 mmol) under an atmosphere of nitrogen gas. The reaction mixture was stirred overnight at RT. Water was added dropwise, and the product was extracted from the reaction mixture with DCM. The organic phase was dried over MgSO4. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (10-40% hexanes/EtOAc). 1-(2-bromo-3-methylphenylamino)-2-methylpropan-2-ol was obtained as a clear colorless oil. the product was extracted from the reaction mixture with DCM The organic phase was dried over MgSO4 The solvent was removed under reduced pressure the remaining residue was purified by flash chromatography (10-40% hexanes/EtOAc)

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

Procedure: To a solution of lithium perchlorate (2.13 g, 20 mmol) in diethyl ether (4 mL) was added 1,2-epoxy-2-methylpropane (0.195 mL, 2.2 mmol), followed by 2-bromo-3-methylaniline (0.250 mL, 2 mmol) under an atmosphere of nitrogen gas. The reaction mixture was stirred overnight at RT. Water was added dropwise, and the product was extracted from the reaction mixture with DCM. The organic phase was dried over MgSO4. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (10-40% hexanes/EtOAc). 1-(2-bromo-3-methylphenylamino)-2-methylpropan-2-ol was obtained as a clear colorless oil. the product was extracted from the reaction mixture with DCM The organic phase was dried over MgSO4 The solvent was removed under reduced pressure the remaining residue was purified by flash chromatography (10-40% hexanes/EtOAc)

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

Procedure: To a solution of potassium tert-butoxide (472 mg, 4.21 mmol) in THF (4 mL) was added a solution of 1-(2-bromo-3-methylphenylamino)-2-methylpropan-2-ol (724 mg, 2.80 mmol) in THF (10 mL), followed by ethyl 2-chloroacetate (0.45 mL, 4.21 mmol). After 1 h at RT an additional 1 eq of potassium t-butoxide (472 mg, 4.21 mmol) and ethyl 2-chloroacetate (0.450 mL, 4.21 mmol) were added. After 6 h water was added, followed by EtOAc. The organic phase was separated, dried over MgSO4 and the solvent was removed under reduced pressure. The remaining residue was purified by flash chromatography (30-80% EtOAc/hexanes). 4-(2-Bromo-3-methylphenyl)-6,6-dimethylmorpholin-3-one was isolated as a light-yellow solid. The organic phase was separated dried over MgSO4 the solvent was removed under reduced pressure The remaining residue was purified by flash chromatography (30-80% EtOAc/hexanes)

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

Procedure: To a solution of lithium perchlorate (2.13 g, 20 mmol) in diethyl ether (4 mL) was added 1,2-epoxy-2-methylpropane (0.195 mL, 2.2 mmol), followed by 2-bromo-3-methylaniline (0.250 mL, 2 mmol) under an atmosphere of nitrogen gas. The reaction mixture was stirred overnight at RT. Water was added dropwise, and the product was extracted from the reaction mixture with DCM. The organic phase was dried over MgSO4. The solvent was removed under reduced pressure and the remaining residue was purified by flash chromatography (10-40% hexanes/EtOAc). 1-(2-bromo-3-methylphenylamino)-2-methylpropan-2-ol was obtained as a clear colorless oil. the product was extracted from the reaction mixture with DCM The organic phase was dried over MgSO4 The solvent was removed under reduced pressure the remaining residue was purified by flash chromatography (10-40% hexanes/EtOAc)