Iodine → HCID 86690451, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1-bromo-3,5-dimethoxybenzene (20 g, 92.1 mmol) in THF (100 ml) was added to a flask (500 ml) with magnesium (2.5 g, 103 mmol), I2 (20 mg) and THF (50 ml) and refluxed for 2 h. The resulting light brown solution was transferred to another flask (500 ml) and was cooled to −78° C. Diethyl phosphorochloridate (17.8 g, 103 mmol) in THF (80 ml) was added at −78° C. within 1 h. The mixture was stirred at −78° C. for 1 h, then slowly warmed up to RT and stirred at RT overnight. Brine (20%, 200 ml) was added to the mixture and it was stirred for 30 min. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (200 ml×1) and CH2Cl2 (100 ml×1). The combined organic layer was washed with brine (300 ml×2) and dried over MgSO4. It was filtered and the solvent was removed. The residues were purified with silica gel pad (eluent: CH2Cl2 to removed impurities, then CH2Cl2/THF=10/1 to wash out the product). The pure product was obtained as pale a yellow oil after the solvent was removed (20.2 g, 80% yield). 1H NMR (300 Mhz, CD2Cl2) δ: 6.90 (dd, J1=2.1 Hz, J2=14.7 Hz, 2H), 6.63 (d, J=2.1 Hz, 1H), 4.05 (quart, J=6.9 Hz, 4H), 3.83 (s, 6H), 1.31 (t, J=6.9 Hz, 6H). 31P NMR (121.5 MHz, CD2Cl2) δ: 19.10.

Provenance & Evidence