Isopropyl Acetate → HCID 12332319, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-amino-2-methyl-1-propanol (488 g, 5.47 mol) in tetrahydrofuran (1.46 L) was added over 35 mins to a solution of potassium tert-butoxide (634 g, 5.65 mol) in tetrahydrofuran (2.95 L) at 2±3° C. The mixture was maintained at this temperature for a further 55 minutes before 4-fluoronitrobenzene (551 mL, 3.90 mol) was added over 1 hour 25 mins keeping the temperature below 10° C. The mixture was warmed to 20±3° C. and stirred for 2 hours. Water (1.95 L) and Isopropyl acetate (1.95 L) were charged to the mixture which was stirred, settled and separated. The organic phase was washed again with water (1.95 L) before 5M hydrochloric acid (1.95 L) was charged, keeping the temperature below 25° C. Isooctane (1.95 L) was added and the layers separated. 5M hydrochloric acid (322 mL) was added to the aqueous phase which was then reduced to approximately 3.9 L by vacuum distillation, causing spontaneous crystallisation, and stirred at room temperature overnight. Filtration, washing with water (2×488 mL) and drying in vacuo at around 48° C. afforded the title intermediate as a white solid (972.1 g, 72% th).

Provenance & Evidence