2-Chloro-5-methylbenzoic acid

Off-white to beige powder

Under nitrogen, 2 mmol of the halogen-substituted benzoic acid indicated in Table 6 was stirred with a solution of 3 mmol Na2CO3 at 50-75 C. until all of the halogen-substituted benzoic acid was dissolved. Subsequently, 0.02 mmol CuSO4 and 0.04 mmol rac-trans-N, N'-dimethylcyclohexane-1, 2-diamine (Ligand F) dissolved in 1 mL deionized water were added and the reaction mixture was heated at 80-100 C. for 4 h. After cooling to ambient temperature the reaction mixtures were carefully acidified with 35% aqueous HCl.In isolation method A, the products were extracted from the aqueous layer twice with ethyl acetate, the ethyl acetate fractions were combined and the crude reaction product was isolated by evaporation of ethyl acetate under vacuum. In isolation method B, the products were isolated by filtration, washed with water and dried under vacuum. The crude reaction product was analyzed by 1H NMR (d6-dmso). The results are summarized in Table 6. TABLE 6 Examples 8~23 Starting material Halogenated Benzoic Acid Isolation CONV SEL Example Benzoic Acid Product T ( C.) Method (%) (%) 8 2, 5-dibromo- 2-hydroxy-5- 80 B >99 >99 bromo- 9 2-bromo-5-nitro- 2-hydroxy-5- 80 B >99 >99 nitro- 10 2-bromo-5-nitro- 2-hydroxy-5- 100 A >99 >99 nitro- 11 2-bromo-5-methyl- 2-hydroxy-5- 80 B >99 >99 methyl- 12 2-bromo-5-methyl- 2-hydroxy-5- 100 A >99 >99 methyl- 13 4-bromo- 4-hydroxy- 100 A >99 >99 14 4-chloro- 4-hydroxy- 80 B >99 >99 15 2, 4-dichloro- 2-hydroxy-4- 100 A 70 >99 chloro- 16 2, 5-dichloro- 2, 5-dihydroxy- 80 B 93 >99 17 2-chloro-5-nitro- 2-hydroxy-5- 100 A 74 >99 nitro- 18 2-chloro-3, 5-dinitro- 2-hydroxy-3, 5- 100 A >99 >99 dinitro- 19 2-chloro-3, 5-dinitro- 2-hydroxy-3, 5- 80 B >99 >99 dinitro- 20 2-chloro-5-methyl- 2-hydroxy-5- 100 A >99 >99 methyl- 21 2-bromo-5- 2-hydroxy-5- 100 A >99 >99 methoxy- methoxy- 22 2-bromo-5- 2-hydroxy-5- 80 B >99 >99 methoxy- methoxy- 23 2-chloro-5-bromo- 2-hydroxy-5- 80 B 73 >99 bromo-7.28 g of 2-amino-5-nitrobenzoic acid, 6.82 g of General procedure: General Experimental Procedures:[0423]To the flask was added 9 (57 mg, 0.2 mmol) , R-COOH (1.2 eq, 0.24 mmol) , EDCI (58 mg, 0.3 mmol) , DMAP (5 mg, 0.04 mmol) in DCM (5 mL) successively, followed by DIPEA (77 mg, 0.6 mmol) with stirring. The resulting mixture was stirred at room temperature for overnight, and purified by column chromatography to give product.Step 1: Weigh out 85 mg (0.5 mmol) of

Molecular Weight:170.59
XLogP3:3.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:170.0134572
Monoisotopic Mass:170.0134572
Topological Polar Surface Area:37.3
Heavy Atom Count:11
Complexity:158
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes