4-FLUORO-3-IODOBENZOIC ACID

light yellow powder

To a solution of 3-amino-4-fluorobenzoic acid (5) (1.00 g, 6.45 mmol) in concentrated aqueous hydrochloric acid solution (37percent, w/w, 8 mL) was added dropwise at -15°C, a solution of sodium nitrite (667 mg, 9.67 mmol) in water (10 mL), while maintaining the temperature below -10 °C. After stirring at -10 °C for 30 min, a solution of potassium iodide (3.21 g, 19.34 mmol) in water (10 mL) was added dropwise, while maintaining the temperature below -5 °C. The resulting solution was warmed to 0 °C and stirred for 30 min, then left at room temperature for 3 h. The reaction was quenched at 0 °C by slow addition of a 10 N aqueous sodium hydroxide solution until pH = 3 followed by 1 M aqueous sodium thiosulfate solution (20 mL). After extraction with dichloromethane (3 x 50 mL), the combined organic layers were washed with water (20 mL), dried over magnesium sulfate, filtered and evaporated under reduced pressure to give 4-fluoro-3-iodobenzoic acid (6) (1.47 g, 5.53 mmol) as an orange solid. Yield 86percent; mp 169-171 °C (litt.[1]: 173-174 °C); IR (KBr) ν 1039, 1291, 1426, 1484, 1585, 1686, 2500-3100 cmHATU (1.7 g, 4.5 mmol) was added to a solution of EXAMPLE 10 4-Fluoro-3-iodobenzoic Acid 4-Fluorobenzoic acid(19.3 g, 137.5 mmol) and iodine(21.2 g, 83.5 mmol) gave

Molecular Weight:266.01
XLogP3:2.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:265.92401
Monoisotopic Mass:265.92401
Topological Polar Surface Area:37.3
Heavy Atom Count:11
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes