2-Amino-2-methyl-1-propanol → 2-(4-Bromo-2-nitro-phenylamino)-2-methylpropan-1-ol

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Reaction Steps

As shown in Scheme ??, mix 5-bromo-2-fluoronitrobenzene (11.2 g, 50.5 mmol) and 2-amino-2-methyl-1-propanol (10.5 mL, 110 mmol) in THF (120 mL). Heat at reflux for 48 h and then cool to room temperature. Remove most of the THF under reduced pressure and then partition the residue between water and EtOAc. Wash the organic layer a second time with water and the dry (MgSO4) and concentrate to give an orange solid. Triturate the solid with hexane (200 mL) and dry to yield 12.95 g (89%) title compound. MS (es) 288 (M−1). HPLC (ISO80-10M) t=2.67 (100%).

Provenance & Evidence