Water → 5-Bromo-1-methyl-2,3-dihydro-1H-indene-1-carboxylic acid

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Reaction Steps

A solution of (rac)-5-bromo-1-methyl-indan-1-carboxylic acid methyl ester (1.318 g, 4.9 mmol) and potassium trimethylsilanolate (3.14 g, 24.5 mmol) in dry THF (25 ml) was stirred at reflux for 1 h. The reaction mixture was allowed to cool to room temperature, water was added and the mixture was extracted two times with tert-butyl methylether. The pH of the aqueous layer was carefully adjusted to 3 by addition of 1N HCl and the aqueous layer was extracted two times with EtOAc. The combined EtOAc-layers were washed with brine, dried with Na2SO4 and evaporated. Toluene was added to the remaining residue and it was evaporated to remove water. The title compound was obtained as light yellow solid (1.204 g, 96%). MS: 252.7 [M−H]−.

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