Sodium Hydroxide → HCID 86708467, compound

Participants

Reaction Steps

(I8A): Methyl 3-bromo-5-((tert-butoxycarbonyl)amino)-4-chlorobenzoate (5 g, 13.71 mmol, Intermediate 4) was dissolved in THF (91 mL) at 0° C. under N2. Lithium aluminum hydride solution (10 ml, 10.00 mmol, 1 M in THF) was added dropwise. The reaction mixture was stirred for 2 hours at which point reaction appeared complete by LC/MS. Water (1.4 mL) was added slowly and resulted in a vigorous quench. 1 M aq. NaOH soln (1.4 mL) was added dropwise, followed by a final addition of H2O (4.2 mL). The mixture was stirred vigorously for 15 minutes and then several scoops of MgSO4 were added. The reaction was diluted with Et2O, stirred for 1 hour and then filtered through celite. Concentrated afforded tert-butyl (3-bromo-2-chloro-5-(hydroxymethyl)phenyl)carbamate (4.08 g).

Provenance & Evidence