Synthesis of N,N-Bis(2-hydroxyethyl)aniline Bromide

The compound was prepared using a reported protocol^{52 (link)} with minor modifications. N,N-Bis(2-hydroxyethyl)aniline (500 mg, 2.8 mmol)
and N-bromosuccinimide (534 mg, 3.0 mmol) were dissolved
in dichloromethane (30 mL), and the mixture was stirred at room temperature
overnight. The solution was washed with a saturated aqueous solution
of sodium bicarbonate (3 × 20 mL) and dried over magnesium sulfate.
The solvent was removed under reduced pressure, and the crude product
purified by silica column chromatography with a linear gradient (0%/100%
to 100%/0% dichloromethane/hexane). The fractions containing the product
were combined, and the compound was dried under vacuum. Yield: 640
mg (2.5 mmol, 88%). ¹H NMR (500 MHz, CD₂Cl₂): δ 7.27 (d, J = 9.1 Hz, 2H), 6.56
(d, J = 9.1 Hz, 2H), 3.77 (t, J =
4.9 Hz, 4H), 3.51 (t, J = 4.9 Hz, 4H). ¹³C{¹H} NMR (125 MHz, CD₂Cl₂): δ
147.3, 132.1, 114.4, 108.5, 60.7, 55.6. HR-MS (m/z): [M + H]⁺ calcd for C₁₀H₁₅BrNO₂, 260.0281; found, 260.0276.