Hydrochloric Acid → 3-Bromo-2,2,3,3-tetrafluoropropylamine

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3-bromo-2,2,3,3-tetrafluoropropylamine was prepared through the intermediate of 4-bromo-4,4,3,3-tetrafluorobutanoic acid (from literature: Wei Yuan, R, Long, L., and Yuan-Fa, Z, Chinese J. Chemistry 1990, 3, 281). The reactions can be described by the following scheme: Na2S2O4/NaHCO3 in CH3CN/H2O BrCF2CF2Br+CH2═CHOEt→BrCF2CF2CH2CHBrOEt CrO3/H2SO4 in CH3COCH3, NaN3/H2SO4; HCl→BrCF2CF2CH2COOH→BrCF2CF2NH3Cl BrCF2CF2COOH (1.2 g, 5 mmol) was dissolved in 3 ml of H2SO4. Sodium azide (0.8 g, 12 mmol) was added in portion to the mixture at 80°. After addition was completed the reaction was continued for 20 hr. The mixture was then cooled to 0°. The solution was diluted with dichloromethane and then sodium carbonate (4 g in 20 ml of water). The organic layer was separated and the water layer was extracted with CH2Cl2 (20 ml×2). The combined dichioromethane was dried over magnesium sulfate overnight and gaseous HCl bubbled into the solution. 0.79 g of white solid was collected by filtration and vacuum dried. 1H NMR δ 3.82 (t, J=16 Hz, 2H). 19F NMR δ −66.8 (t, J=16 Hz, 2H), −113.74 (m, 2F). Chemical analysis: Calculated for C3H5BrClF4BN C: 14.6, H: 2.03, N:5.68. Found C: 14.57, H: 1.96, N: 5.56.

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