4-Fluoro-2-iodo-6-methylbenzoic acid synthesis

Yield:1048025-60-0 130 g

Reaction Conditions:

with [bis(acetoxy)iodo]benzene;iodine;palladium diacetate in N,N-dimethyl-formamide at 100; for 48 h;

Steps:

97 Reference Example 97 4-fluoro-2-iodo-6-methylbenzoic acid

A solution of 4-fluoro-2-methylbenzoic acid (80 g), iodobenzene diacetate (234 g), palladium(II) acetate (5.82 g) and iodine (264 g) in DMF (1000 mL) was stirred at 100°C for 2 days. The reaction solution was diluted with saturated aqueous sodium sulfite solution and methyl tert-butyl ether, and the organic layer was separated, washed with 2N sodium hydroxide, and adjusted to pH=3-4 with 1N hydrochloric acid. The organic layer was separated, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by silica gel chromatography (petroleum ether-ethyl acetate) to give the title compound (130 g). ¹H NMR (400 MHz, DMSO-d₆) δ 2.31 (3H, s), 7.20 (1H, dd, J = 10.0, 2.0 Hz), 7.59 (1H, dd, J = 8.0, 2.4 Hz).

References:

EP2921480,2015,A1 Location in patent:Paragraph 0505; 0506