2-Methyl-2-butene → 4-Amino-3-chloro-6-propyl-5-fluoropicolinic acid

Participants

Reaction Conditions

Reaction Steps

A microwave vial equipped with a magnetic stir bar was charged with 4-amino-3-chloro-6-propyl-5-fluoropicolinaldehyde (15.9 mg, 0.072 mmol) and t-butanol (1.0 mL). The mixture was treated with H2O (0.40 mL), 2-methylbut-2-ene (100 μL, 0.10 mmol), sodium hydrogenphosphate (21.6 mg, 0.100 mmol), and finally sodium chlorite (19.28 mg, 0.206 mmol) was added in one portion. The mixture was heated to 85° C. for 16 h. An aliquot of the reaction mixture was analyzed by LC-MS. LC-MS analysis showed one major product with the correct mass for the desired product. The reaction mixture was evaporated to dryness under N2. Purification via reverse phase chromatography yielded 4-amino-3-chloro-6-propyl-5-fluoropicolinic acid (4.7 mg, 27.9%): 1H NMR (400 MHz, CDCl3) δ 11.60 (s, 1H), 4.98 (m, 2H), 2.76 (m, 2H), 1.75 (m, 2H), 0.99 (m, 3H); 19F NMR (376 MHz, CDCl3) δ−139.98; ESIMS m/z 231.2 ([M−H]−).

Provenance & Evidence