3-Methoxyphenylacetylene

To a solution of CBr4 (9.70 g, 29.4 mmol) in CH2Cl2 was added PPh3(15.4 g, 5.90 mmol) in CH2Cl2 at 0oC. After the stirring for 5 min, the solution wasadded m-anisaldehyde (1.99 g, 7.30 mmol) and stirred for 20 min. H2O and CH2Cl2were added to the solution. Organic layer was washed with saturated NaHCO3 and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by columnchromatography (hexane) to give 2’, 2’-dibromovinyl-3-methoxybenzene (2.00 g, 6.80mmol, 92percent) as a colorless oil. 1H NMR (CDCl3, 400 MHz): δ=3.82 (s, 3H), 6.91 (dd, 1H, J=8.2, 2.3 Hz), 7.12 (d, 1H, J=8.2 Hz), 7.15 (d, 1H, J=2.3 Hz), 7.29 (t, 1H, J=8.2Hz), 7.48 (s, 1H). To a solution of 3-(2’, 2’-dibromovinyl)methoxybenzene (1.80 g, 6.20mmol) in THF was added n-BuLi (2.6 M in hexane; 5.00 ml, 12.9 mmol) at -78oC. Afterthe stirring for 15 min, saturated NH4Cl was added to the solution and the mixture waswarmed to room temperature. The mixture was extracted with Et2O. Organic layer waswashed with saturated NaHCO3 and brine, dried over MgSO4 and evaporated in vacuo.The residue was purified by column chromatography (hexane:AcOEt=10:1) to give 8(472 mg, 3.57 mmol, 58percent) as a colorless oil.In this step, (3-Methoxy-phenylethynyl) -trimethyl-silane was dissolved in MeOH (100mL) and added to K2C03 (2.45 g, 17.7 mmol). The reaction mixture was stirred at room temperature for 1 h and then filtrated. The filtrate was concentrated under reduced pressure. The residue was dissolved in Et20 (100 mL) and washed with citric acid (20percent, 100 mL), saturated NHCO3 (lOOmL), H20 and then concentrated under reduced pressure. The combined organic layers were washed with brine, dried over MgS04 and then concentrated. The residue was purified by flash column chromatography (1percent EtOAc in hexane) to afford 685 mg of product (43percent) as a pale yellow oil. lH NMR (CDCl3) : 4 3.83 (s, 3H), 6.92-6. 96 (m, 1H), 7.05-7. 06 (m, 1H), 7.11-7. 14 (m, 1H), 7. 24-7. 29 (m, 1H).

Molecular Weight:132.16
XLogP3:2.5
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:132.057514874
Monoisotopic Mass:132.057514874
Topological Polar Surface Area:9.2
Heavy Atom Count:10
Complexity:142
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes