Water → HCID 43560401, compound

Participants

Reaction Conditions

Reaction Steps

To 5-bromo-2-hydroxybenzaldehyde (1.00 g, 4.97 mmol, 1.00 equiv) and K2CO3 (3.44 g, 24.9 mmol, 5.00 equiv) in THF (10 mL) in an oven-dried round-bottom flask fitted with a reflux condenser under a N2 atmosphere at 23 ° C. was added (bromomethyl)cyclopropane (1.01 g, 0.724 mL, 7.46 mmol, 1.50 equiv). The reaction mixture was warmed in an oil heating bath at a temperature of 70 ° C. and heated at reflux with vigorous stirring for 40 hours. The reaction mixture was cooled to 23 ° C. and poured into H2O (30 mL) in a separatory funnel. CHCl3 (30 mL) was added, the funnel was shaken and the organic phase collected. The aqueous phase was then extracted with CHCl3 (2×30 mL). The combined organic phases were washed with brine (30 mL), dried with Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel, eluting with 2-7% EtOAc in hexanes (v/v) to afford 1.05 g of the title compound as a colorless solid (83% yield). Rf=0.30 (hexanes/EtOAc 19:1 (v/v)). NMR Spectroscopy: 1H NMR (600 MHz, CDCl3, 23 ° C., δ): 10.45 (s, 1H), 7.91 (d, J=2.5 Hz, 1H), 7.58 (dd, J=8.9, 2.6 Hz, 1H), 6.84 (d, J=8.9 Hz, 1H), 3.91 (d, J=7.2 Hz, 2H), 1.32-1.26 (m, 1H), 0.71-0.63 (m, 2H), 0.41-0.34 (m, 2H). 13C NMR (125 MHz, CDCl3, 23 ° C., δ): 188.7, 160.5, 138.3, 130.9, 126.5, 115.0, 113.5, 73.9, 10.1, 3.4. HRMS-FIA (m/z): calcd for C11H11BrNaO2[M+Na]+, 276.9840; found, 276.9820.

Provenance & Evidence