2-Bromo-5-chloronitrobenzene → 7-bromo-4-chloro-1H-indole

温度

-40 °C

1.19 g (5 mmol) of 2-bromo-5-chloro-nitrobenzene were dissolved in 50 ml THF. At a temperature of −45° C. 15 ml of a 1M vinyl magnesium bromide solution in THF were added under nitrogen in such a way that the temperature did not exceed −40° C. After complete addition the dark solution was stirred for 30 min at −40° C. The reaction mixture was quenched with 10 ml aqueous saturated ammonium chloride solution and extracted twice with diethyl ether. The combined organic layers were washed once with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated. The residue was purified by column chromatography (100 g silica gel; heptane/EtOAc 19:1) to yield 562 mg (49%) of 7-bromo-4-chloro-1H-indole as an orange oil. MS (EI) 229.0 (80), 231.0 (100), 233.0 (30) (M)+.

1. customAt a temperature of −45° C
2. customdid not exceed −40° C
3. additionAfter complete addition the dark solution
4. customThe reaction mixture was quenched with 10 ml aqueous saturated ammonium chloride solution
5. extractionextracted twice with diethyl ether
6. washThe combined organic layers were washed once with saturated aqueous sodium chloride solution
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. customthe solvent was evaporated
10. customThe residue was purified by column chromatography (100 g silica gel; heptane/EtOAc 19:1)

ORDレコード

ord-d0f4edee0dd4404c9182bf47efb1d10d

出典データセット

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07259183B2