Ethyl 2-iodobenzoate

General procedure: Iodobenzoic acid (10 g) was added to 60 mL of alcohol derivatives (methanol, ethanol, n-butanol, iso-butanol and sec-butanol) in 5 mL conc. HEthanol (50.0 mL), H2SO4 (0.5 mL) and 2-iodobenzoic acid (2.00 mg, 8.06mmole) were added into an oven-dried 100 mL round-bottomed flask. Thereaction was run at 78 °C for 2.5 hours. After the reaction was complete, thesolvent was removed in vacuo by rotary-evaporatory. The resulting residue was diluted withethyl acetate (30 mL) and then washed with saturated sodium bicarbonate solution (40 mL). Theaqueous phase was then extracted with ethyl acetate (30 mL). The combined organic layers werewashed with water (30 mL) followed by drying over MgSO4 and concentration in vacuo usingrotary-evaporator. The desired product (1.94 g, 88 percent) was obtained as light yellow oil withoutfurther purification: IR (ZnSe) ν (cm-1): 3062 (w), 2980 (m), 1719 (s), 1101 (s), 1561 (s), 1042(s), 737 (s), 686 (s); 1H NMR (300 MHz, CDCl3) δ 1.42 (t, J = 7.2, 3H), 4.41 (q, J = 7.2, 2H), 7.15 (dt, J = 7.2, 1.5, 1H), 7.41 (dt, J = 7.5, 1.2, 1H), 7.99 (dd, J = 7.8, 0.9, 1H), 7.80 (dd, J =7.5, 1.5, 1H); 13C NMR (300 MHz, CDCl3) δ 13.6, 60.5, 93.9, 127.0, 130.7, 131.1, 136.1, 143.2, 167.0.Ethyl 2-iodobenzoate 4d was prepared from esterification of corresponding halo-acid by refluxing in ethanol for 24 h. Pure product was obtained in 85percent yield by column chromatography using dichloromethane as eluent.General procedure: In a 50 mL two-necked round-bottomed flask equipped with a magnetic stirring bar, a reflux condenser and a calcium chloride drying tube was placed nicotinic acid (1 g, 8.1 mmol) suspended in boron trifluoride etherate (10 mL). The reaction mixture was stirred and heated to 120 °C overnight during which the creamy reaction mixture changed into a brownish solution. Thin layer chromatography (hexane/ethyl acetate 3:1) revealed complete reaction. The cooled reaction mixture was diluted with water (25 mL) and extracted with ethyl acetate (3 x 10 mL). The combined organic extract was washed to the end of effervescence with a saturated solution of NaHCO3. The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo giving a crude yield of 1.11 g (92percent).

Molecular Weight:276.07
XLogP3:3.1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:275.96473
Monoisotopic Mass:275.96473
Topological Polar Surface Area:26.3
Heavy Atom Count:12
Complexity:159
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes