Bromide ion → 4-Heptanol, 1,1,1,7,7,7-hexafluoro-

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Reaction Steps

3-Bromo-1,1,1-trifluoropropane (31 g, 0.175 mol) was dissolved in THF (175 mL). Mg (4.2 g, 0.175 mol) was placed in a 1 L, 3-necked round-bottom flask equipped with a condenser, nitrogen inlet and thermometer. The bromide solution (10 mL) was added to cover the magnesium and upon stirring a mild exotherm commenced. The temperature was kept <40° C. by immersing the flask in a bowl of water. The bromide was added slowly to maintain this mild exothermic reaction. When the exotherm had subsided the mixture was cooled in ice-water and methyl formate (7 mL, 0.11 mol) in THF (175 mL) was added. The mixture was stirred for 30 min and then quenched with NH4Cl (aq.soln. 100 mL). The mixture was extracted with ethyl acetate. The organic extracts were washed with brine, dried (MgSO4) and evaporated.

Provenance & Evidence