Dichloromethane → METHYL 3-PHENYLETHYNYL-BENZOATE

Participants

Reaction Steps

Methyl 3-iodobenzoate, phenylacetylene (1.5 eq.) and Pd(PPh3)2Cl2 (5 mol %) in piperidine (3 eq.) was heated at 70° C. for 30 minutes. The solidified residue was dissolved with CH2Cl2 and water and poured onto HCl 2N. The acidic phase was extracted three times with CH2Cl2. The combined organic layers were washed twice with HCl 2N, once with water and once with brine. The organic layer was then dried over MgSO4 and concentrated. The resulting residue was purified using SiO2 with petroleum spirit/toluene 70:30 to give methyl 3-phenylethynyl-benzoate as a white solid (quantitative yield). NMR 1H (ppm, CDCl3): 8.20 (t, J4=1.7 Hz, 1H), 7.98 (d, J3=7.9 Hz, 1H), 7.69 (d, J3=7.6 Hz, 1H), 7.54-7.50 (m, 2H), 7.42 (t, J3=7.8 Hz, 1H), 7.36-7.31 (m, 3H), 3.92 (s, 3H).

Provenance & Evidence