[F:1][C:2]([F:6])([CH3:5])[CH2:3][OH:4].[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([S:16](Cl)(=[O:18])=[O:17])=[CH:12][CH:11]=1)([O-:9])=[O:8].C(N(CC)CC)C>C1COCC1.CN(C)C1C=CN=CC=1.CC(OC)(C)C.O>[N+:7]([C:10]1[CH:11]=[CH:12][C:13]([S:16]([O:4][CH2:3][C:2]([F:6])([F:1])[CH3:5])(=[O:18])=[O:17])=[CH:14][CH:15]=1)([O-:9])=[O:8]
2,2-Difluoropropan-1-ol (383 mg, 3.99 mmol) was combined with THF (3 mL). The solution was stirred at room temperature as 4-nitrobenzene-1-sulfonyl chloride (931 mg, 4.20 mmol) was added followed by triethylamine (0.611 mL, 4.39 mmol). After about 28 hours, the reaction mixture was diluted with THF (2 mL) and 4-dimethylaminopyridine (23 mg, 0.188 mmol) was added. After 16 hours the reaction mixture was diluted with 12 mL MTBE and 5 mL water and stirred for 5 minutes before the layers were separated. The organic layer was extracted with 1 M HCl (3 mL), 5% sodium carbonate (3 mL), brine (3 mL), and then water (3 mL). The organic layer was diluted with another 10 mL MTBE and extracted three times with 1 M NaOH (5 mL) and then water (5 mL). The organic layer was dried over sodium sulfate, filtered, concentrated on a rotovap, and dried under vacuum to give 2,2-difluoropropyl 4-nitrobenzenesulfonate (526 mg) as a pale yellow solid.
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