Phenethyl bromide → HCID 22716779, compound

Participants

Reaction Steps

(2-Bromoethyl)benzene (41 mL, 0.3 mol, 5 eq) was added to a stirred solution of 5-formylsalicylic acid (10 g, 0.06 mol, 1 eq), tetra-n-butylammonium iodide (44 g, 0.12 mol, 2 eq) and cesium carbonate (39 g, 0.12 mol, 2 eq) in N,N-dimethylformamide (200 mL). The reaction mixture was stirred for 4 days, then concentrated in vacuo. The residue was diluted with ethyl acetate (200 mL) and the organic solution washed with water (200 mL), 1M HCl (2×200 mL), 1M sodium hydroxide (2×200 mL) and then brine (200 mL), dried over sodium sulfate and evaporated in vacuo to give a brown oil. The product was not purified further, but taken immediately onto the next step. RF (petroleum ether:ethyl acetate, 1:1) 0.88. 1H NMR (CDCl3) δ9.88 (s, 1H, O═C—H), 8.23 (d, 1H, J 2.2 Hz, ArH), 7.98 (dd, 1H, J 8.7 and 2.2 Hz, ArH), 7.06 (d, 1H, J 8.7 Hz, ArH), 4.56 (t, 2H, J 7.2 Hz, OCH2CH2Ph), 4.33 (t, 2H, J 7.2 Hz, OCH2CH2Ph), 3.11 (t, 2H, J 7.2 Hz, OCH2CH2Ph), 3.03 (t, 2H, J 7.2 Hz, OCH2CH2Ph).

Provenance & Evidence