Water → 2-Bromo-5,6-dichloro-indan-1-ol

Temperature

25 °C

According to Scheme 2, step IV: To a solution of 5,6-dichloro-1H-indene (5f) (1.28 g, 6.92 mmol), which was obtained according to Scheme 2 by following a reaction sequence according to synthesis of (5a), in dimethylsulfoxide (6.5 ml) and water (0.16 ml) N-bromosuccinimide (2.44 g, 13.7 mmol) was added at 10° C. and the mixture was stirred at 25° C. for 1 h. The mixture was poured on water, stirred for 30 min and the solid material was filtered off. The crude product was purified by silica gel chromatography (eluting with 0 to 50% ethyl acetate in heptane) to give 1.46 g of 2-bromo-5,6-dichloro-indan-1-ol which was immediately dissolved in tetrahydrofuran (35 ml). Finely powdered NaOH (1.37 g, 34.2 mmol) was added and the mixture was stirred at 25° C. for 2 h. The mixture was filtered through a short pad of celite and washed with a small amount of ethyl acetate. The filtrate was evaporated to dryness to give 1 g of racemic(1aS,6aR)-3,4-Dichloro-6,6a-dihydro-1aH-1-oxa-cyclopropa[a]indene (6f), which was used in the next step without purification.

1. additionThe mixture was poured on water
2. stirringstirred for 30 min
3. filtrationthe solid material was filtered off
4. customThe crude product was purified by silica gel chromatography (eluting with 0 to 50% ethyl acetate in heptane)

ORD record

ord-aca68ae87b474e27b646d1bba1623170

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09034897B2