DifluoroiodoMethyl phenyl sulfone synthesis
- Product Name:DifluoroiodoMethyl phenyl sulfone
- CAS Number:802919-90-0
- Molecular formula:C7H5F2IO2S
- Molecular Weight:318.08
1535-65-5
802919-90-0
Difluoromethyl phenyl sulfone (192 mg, 1 mmol) and elemental iodine (508 mg, 4 mmol) were dissolved in DMF (4 mL) in a Schlenk flask under argon protection. The system was cooled to -30 °C and a solution of t-BuOK (448 mg, 4 mmol) in DMF (4 mL) was added slowly dropwise via syringe. The reaction temperature was maintained between -30 °C and -20 °C with continuous stirring for 1 h. The reaction progress was monitored by 19F NMR tracking. Upon completion of the reaction, the reaction was quenched by the addition of 1N HCl aqueous solution (5 mL) at -50 °C, followed by slow warming to room temperature. Saturated aqueous NaCl solution (10 mL) was added and the reaction mixture was extracted with ether (15 mL x 3). The organic phases were combined, dried with anhydrous MgSO4, filtered and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=9:1) to afford the target product difluoroiodomethyl phenyl sulfone (294 mg, 92% yield), which is a colorless solid and turns red easily when exposed to light. The product characterization data were as follows: 1H NMR (500 MHz, CDCl3): δ 7.63 (t, J = 7.4 Hz, 2H), 7.79 (t, J = 7.4 Hz, 1H), 7.99 (d, J = 7.5 Hz, 2H); 13C NMR (125 MHz, CDCl3): δ 102.5 (t, J = 355 Hz), 128.1, 129.7, 131.3, 136.1; 19F NMR (470 MHz, CDCl3): δ -52.2; MS (EI, m/z): 318 (M+), 177, 142, 127; HRMS (EI): m/z calcd for C7H5F2IO2S (M+) 317.9023, found 317.9013. found 317.9013.
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Yield:-
Steps:
Multi-step reaction with 2 steps
1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere
2.1: copper(l) iodide; cesium fluoride / N,N-dimethyl-formamide / 4 h / -30 °C
2.2: 16 h / 0 °C / In air
References:
Zhu, Jieming;Wang, Fei;Huang, Weizhou;Zhao, Yanchuan;Ye, Wenchao;Hu, Jinbo [Synlett,2011,# 7,p. 899 - 902]
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