2-Amino-2-methyl-1-propanol → 2-bromo-N1,N4-bis(1-hydroxy-2-methylpropan-2-yl)terephthalamide

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Reaction Steps

2-Bromoterephthalic acid (750 mg, 3.06 mmol, 1 eq.) was suspended into SOCl2 (5 ml) in the presence of DMF (1 drop), and the solution was refluxed for 3 hr. After cooling to room temperature, evaporating and dried in vacuo, the resulting compound was dissolved in CH2Cl2 (10 ml), and was dropped into a solution of 2-amino-2-methylpropan-1-ol (750 mg, 8.41 mmol, 2.7 eq.) and DIEA (1.5 ml) in CH2Cl2 (10 ml), and the solution was stirred at room temperature overnight. Saturated NaHCO3 aqueous solution was added to the reaction mixture and extracted with EtOAc (×3), and combined organic phase was washed with water and brine, dried over Na2SO4, filtered and evaporated to obtain 2-bromo-N1,N4-bis(1-hydroxy-2-methylpropan-2-yl)terephthalamide 4b as a white solid. (922 mg, 78%)

Provenance & Evidence