methyl 5-bromo-2,3-dihydro-1H-indene-1-carboxylate

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Lithium bis(trimethylsilyl)amide (6.16 ml, 6.16 mmol, 1M solution in THF) was added dropwise to a solution of (rac)-5-bromo-indan-1-carboxylic acid methyl ester (1.31 g, 5.14 mmol) in dry THF (25 ml) at −78° C. After the addition was completed, the solution was stirred at −78° C. for 45 minutes. Then, iodomethane (2.19 g, 959 μl, 15.4 mmol) was added, the solution was allowed to warm to room temperature and stirred for 48 h. The reaction was quenched by addition of sat. NH4Cl solution and extracted two times with EtOAc. The combined organic layers were washed with brine, dried with Na2SO4 and evaporated. The remaining yellow oil was purified by chromatography (silica gel; heptane/EtOAc 95:5) to obtain the title compound as yellow oil (1.319 g, 95%). MS: 269.2 [M+H]+. After the addition to warm to room temperature stirred for 48 h The reaction was quenched by addition of sat. NH4Cl solution extracted two times with EtOAc The combined organic layers were washed with brine dried with Na2SO4 evaporated The remaining yellow oil was purified by chromatography (silica gel; heptane/EtOAc 95:5)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (rac)-5-bromo-indan-1-carboxylic acid (1.326 g, 5.5 mmol) in MeOH (55 ml) was treated with 4N HCl in dioxane (15 ml) and the mixture was stirred at reflux for 7 h. The yellow solution was allowed to cool to room temperature and all volatiles were removed. The remaining brown oil was purified by chromatography (silica gel; heptane/EtOAc 95:5) to obtain the title compound as light yellow oil (1.31 g, 93%). at reflux for 7 h all volatiles were removed The remaining brown oil was purified by chromatography (silica gel; heptane/EtOAc 95:5)