Water → 2-Fluoro-3-iodo-4-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-fluoro-3-iodo-4-methylbenzonitrile (3.9385 g, 11.316 mmol; 76% mass % pure) in 1,4-dioxane (10.0 mL, 128 mmol) was added water (4.0 mL, 220 mmol) and sulfuric acid (6.0 mL, 110 mmol). The reaction mixture was heated at 110° C. for 20 hours. The reaction mixture was cooled to room temperature and then poured into ˜200 mL ice water. The resulting tan precipitate was collected by filtration, washed with water and ethyl acetate, and dried under vacuum to provide the title product. The filtrate was transferred to a separatory funnel, and the ethyl acetate layer was separated, washed with brine, dried over MgSO4, and evaporated in vacuo to yield additional desired product for a combined yield of 3.8743 g which was carried forward without purification.

Provenance & Evidence