Methanol → t-Butyl 2-(2-bromo-4-((methylamino)methyl)phenoxy)acetate

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Reaction Steps

t-Butyl 2-(2-bromo-4-formylphenoxy)acetate (1) (10.11 g, 32.1 mmol, 1 eq) was dissolved in a 2 M solution of methylamine in methanol (30 mL, 60 mmol, 1.9 eq) and stirred at room temperature for 4 h. The solvent and excess methylamine were removed in vacuo and the resultant imine was dissolved in anhydrous methanol (200 mL). Sodium Borohydride (2.4 g) was added slowly under argon and the mixture was stirred for 2 h. Saturated NaHCO3 (100 mL) was added and allowed to stir for 15 minutes at which point the methanol was removed in vacuo. The resultant aqueous mixture was extracted with DCM (2×50 mL) and the combined organic layers were washed with brine (100 mL), dried (Na2SO4) and concentrated in vacuo to yield 6.2 g (58%) of t-butyl 2-(2-bromo-4-((methylamino)methyl)phenoxy)acetate (2). 1HNMR (CDCl3, 300 MHz): δ 7.50 (d, 1H), 7.15 (m, 1H), 6.72 (d, 1H), 4.55 (s, 2H), 3.65 (s, 2H), 2.41 (s, 3H), 1.45 (s, 9H).

Provenance & Evidence