Hydrogen Bromide → HCID 57559193, compound

Participants

Reaction Steps

A solution of the product from Step 2 (14.2 g, 57.9 mmol) in a 5:1 methanol/H2O solvent mixture (240 mL) was stirred as lithium hydroxide mono-hydrate (7.29 g, 174 mmol) was added. After stirring at room temperature for 2 h, the reaction volume was concentrated and the remainder was partitioned between dichloromethane (300 mL) and 4N HCl (100 mL). The organic phase was separated, dried over sodium sulfate and concentrated to afford 8.60 g (68%) of the product as a white solid. This product contains 33% of the 5-chloro adduct. 1H NMR (400 MHz, Chloroform-d) δ 3.67 (t, 0.6H), 3.53 (t, 1.4H), 2.62 (t, 2H), 2.43-2.28 (m, 2H). 5-Chloro-4,4-difluoro-pentanoic acid can be prepared in an analogous fashion by substituting HCl in dioxane for the HBr in acetic acid in Step 1.

Provenance & Evidence