Aluminium lithium hydride → 4-(2-((4-Bromophenyl)amino)ethoxy)phenol

Participants

Reaction Steps

Compound 7b (80 mg, 0.25 mmol) was dissolved in THF (5 ml). LiAlH4 (30 mg, 0.5 mmol) was added portionwise and the reaction was refluxed for 6 hrs. The reaction was quenched slowly with water, 10% sodium hydroxide, and then water again. The aqueous layer was extracted with EtOAc (2×50 mL). The organic was concentrated to yield compound 7 (10 mg, 0.03 mmol, 13% yield). 1H NMR (CDCl3, 400 MHz) δ 7.29 (m, 2H), 6.80 (q, 4H), 6.56 (d, 2H), 4.81 (broad s, 1H), 4.13 (t, 2H), 3.47 (t, 2H); HRMS (ESI, positive) m/z calcd. for C14H14BrNO2 [M+H]+: 308.0286, found: 308.0261.

Provenance & Evidence