Hydrogen Bromide → HCID 86750950, compound

Participants

Reaction Conditions

Reaction Steps

A 2-L, 3-neck, jacketed flask fitted with a mechanical stirrer, thermocouple probe, and an addition funnel was charged with 48% hydrobromic acid (208.0 g, 1.23 mole). The flask was cooled to 5° C. by circulating coolant through the jacket, and 3-heptafluorobutoxymethyl-3-methyloxetane was added at a rate to maintain the temperature below 12° C. The addition was complete after 11/4 hours. GC analysis indicated 98% conversion of the starting material to product. Additional 48% HBr (14.9 g, 0.088 mole) was added, and the mixture was stirred overnight at room temperature. The mixture was poured into 200-ml water, and the pH of the aqueous layer was adjusted to a pH of about 5 with 1N NaOH. The layers were separated, and the organic layer was washed with water (250 ml), dried (MgSO4), and filtered to give 300.4 g (93.5%) of 3-bromo-2-heptafluorobutoxymethyl-2-methyl-1-propanol (2), a clear oil: 1H NMR (CDCl3) 1.00 (s), 3.43 and 3.52 (AB, J=10.4 Hz), 3.53 and 3.59 (AB, J=11.1 Hz), 3.58 (s), and 3.95 (t, J=13.4 Hz); Anal. Calcd for C9H12BrF7O2 : C, 29.60; H, 3.32; Br, 21.88; Found: C, 29.15; H, 3.27; Br, 21.09.

Provenance & Evidence