Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → HCID 67512930, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(3-hydroxypropyl)-2-iodophenol (Step A) (2.94 g, 10.57 mmol), 2-chloroethyl p-toluenesulfonate (2.88 ml, 15.86 mmol), and potassium carbonate (3.65 g, 26.4 mmol) in DMF (11 ml) was heated at 50° C. under nitrogen overnight. EtOAc was added and the mixture was washed 2 times with water, followed by brine. The organic layer was dried over sodium sulfate, filtered, and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with EtOAc in hexanes to afford the title compound. 1H NMR (500 MHz, CD3OD): δ 7.62 (d, J=2.1 Hz, 1H); 7.18-7.13 (m, 1H); 6.85 (d, J=8.3 Hz, 1H); 4.24 (t, J=5.5 Hz, 2H); 3.86 (t, J=5.5 Hz, 2H); 3.54 (t, J=6.4 Hz, 2H); 2.59 (t, J=7.7 Hz, 2H); 1.77 (p, J=7.2 Hz, 2H).

Provenance & Evidence