Hydrochloric Acid → 6-Bromo-2,3-dihydro-1H-indene-1-carboxylic acid

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Reaction Steps

By following the procedure of Tetsuya, et al. referenced in part A, the 6-bromo compound can be obtained. For example, to a stirred, ice-cooled mixture of 8.1 g (50 mmol) indane-1-carboxylic acid and 8.1 g of FeCl3 in 300 ml of CCl4 is added dropwise a solution of 8.8 g of Br2 in 100 ml methylene chloride over a 1 hour period. The mixture is stirred for 3 hours under cooling and then for 1.5 hours at room temperature. The mixture is poured into 500 ml of dilute HCl and extracted with CHCl3. The extract is washed with water, dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue is crystallized from hexane to give 6-bromo-indane-1-carboxylic acid.

Provenance & Evidence