Water → HCID 178519456, compound

Participants

Reaction Conditions

Reaction Steps

Ferrocene (10.0 g, 53.8 mmol) was dissolved in CH2Cl2 (50 mL) in a 250 mL round-bottom flask with argon inlet and dripping funnel and cooled to 0° C. Then aluminum (III) chloride (7.88 g. 59.1 mmol) was suspended in CH2Cl2 (50 mL) in a dropping funnel and o-bromobenzoyl chloride (12.4 g, 7.4 mL, 56.4 mmol) was added dropwise using a syringe. The resulting solution was added by drops of the ferrocene from the dropping funnel. An intense dark purple color appeared. After 2 h of stirring water (15 mL) was slowly added at 0° C. After the end of the hydrolysis, which progressed with strong generation of Gases, the solution was diluted with CH2Cl2 (100 mL) and washed with potassium carbonate solution (50 mL) and a saturated salt solution (50 mL). The organic phase was dried over magnesium sulfate, filtered and concentrated on a rotary evaporator. The crude product was purified by column chromatography (pentane/tert-butylmethyl ether=4/1). Ketone 1 (16.1 g, 43.6 mmol), 81%) was obtained as a dark red solid (mp: 102° C.).

Provenance & Evidence