Benzoic acid, 3,4-dichloro-, ethyl ester

General procedure: Aldehyde 1 (1.0 mmol; 1.0 equiv.) and 4 Å molecular sieves (300 mg) were added to a mixture of DMF (3.0 mL) and an appropriate alcohol (or a thiol) (3.0 mL). To the above solution was added sodium cyanide (1.5 mmol; 1.5 equiv). The reaction mixture was stirred in an open flask at 50 C and monitored by TLC. After the complete consumption of 1, the mixture was poured into water (25 mL) and extracted with diethyl ether (5 × 10 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated. The crude mixture was further purified by column chromatography on silica gel using ethyl acetate/hexane as the eluent to furnish the desired ester compound 3. The aqueous layer was acidified with HCl, extracted with ether, and concentrated to yield the corresponding carboxylic acid 6, which was sufficiently pure needing no further purification.General procedure: Sulfonimidate 1 (0.859 g, 3.00 mmol) and 2-bromobenzoic acid (0.601 g, 3.00 mmol) were refluxed in THF (25 mL) for 5 d. TLC analysis (hexane–EtOAc, 6:1) showed that most of 1 had been converted into the sulfonamide 2. The mixture was concentrated by rotary evaporation and pentane (5 mL) was added. The pentane solution was removed by pipet and treated with NaH to precipitate any unreacted acid and residual 2. This solution was pipet filtered, concentrated in vacuo and purified by Kugelrohr distillation; yield: 0.32 g (47percent). IR and General procedure: Aldehyde 1 (1.0 mmol; 1.0 equiv.) and 4 Å molecular sieves (300 mg) were added to a mixture of DMF (3.0 mL) and an appropriate alcohol (or a thiol) (3.0 mL). To the above solution was added sodium cyanide (1.5 mmol; 1.5 equiv). The reaction mixture was stirred in an open flask at 50 C and monitored by TLC. After the complete consumption of 1, the mixture was poured into water (25 mL) and extracted with diethyl ether (5 × 10 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, and concentrated. The crude mixture was further purified by column chromatography on silica gel using ethyl acetate/hexane as the eluent to furnish the desired ester compound 3. The aqueous layer was acidified with HCl, extracted with ether, and concentrated to yield the corresponding carboxylic acid 6, which was sufficiently pure needing no further purification.General procedure: Sulfonimidate 1 (0.859 g, 3.00 mmol) and 2-bromobenzoic acid (0.601 g, 3.00 mmol) were refluxed in THF (25 mL) for 5 d. TLC analysis (hexane–EtOAc, 6:1) showed that most of 1 had been converted into the sulfonamide 2. The mixture was concentrated by rotary evaporation and pentane (5 mL) was added. The pentane solution was removed by pipet and treated with NaH to precipitate any unreacted acid and residual 2. This solution was pipet filtered, concentrated in vacuo and purified by Kugelrohr distillation; yield: 0.32 g (47percent). IR and

Molecular Weight:219.06
XLogP3:4.2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:217.9901349
Monoisotopic Mass:217.9901349
Topological Polar Surface Area:26.3
Heavy Atom Count:13
Complexity:185
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes