Potassium Carbonate → 3-fluoro-N-(3-iodo-4-methylphenyl)-4-methylbenzamide

Temperature

0 °C

A stirred suspension of 3-fluoro-4-methyl benzoic acid (1.15 g, 7.44 mmol) in CH2Cl2 (50 mL) and DMF (2 drops) was cooled to 0° C. under argon and treated with oxalyl chloride (0.71 mL, 8.18 mmol) dropwise. The mixture was warmed to r.t. and stirred for 1 h. In a separate flask, 3-iodo-4-methyl aniline (2.60 g, 11.16 mmol), K2CO3 (1.54 g, 8.93 mmol) and pyridine (4 drops) were suspended in CH2Cl2 (10 mL). The mixture was cooled to 0° C. under argon and the acid chloride reaction mixture was slowly added. Upon complete addition, the reaction mixture was allowed to warm to room temperature and stirred for 3 days. The resultant solid was filtered off and the reaction mixture was diluted with EtOAc. The organic phase was washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo. Diethyl ether was added and the impurities were filtered off, affording the title compound as a brown solid. 1H-NMR (400 MHz, d6-DMSO) δ: 10.24 (1H, s), 8.32 (1H, d), 7.77 (3H, m), 7.46 (1H, t), 7.32 (1H, t), 2.35 (3H, s), 2.32 (3H, s).

1. temperatureThe mixture was warmed to r.t.
2. temperatureThe mixture was cooled to 0° C. under argon
3. additionwas slowly added
4. additionUpon complete addition
5. temperatureto warm to room temperature
6. stirringstirred for 3 days
7. filtrationThe resultant solid was filtered off
8. additionthe reaction mixture was diluted with EtOAc
9. washThe organic phase was washed with water, brine
10. dry with materialdried (Na2SO4)
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. additionDiethyl ether was added
14. filtrationthe impurities were filtered off

ORD record

ord-02742f734f2746269c55470e1a45662b

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07674789B2