t-Butyl bromide → HCID 44622906, compound

HRID 468312Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[Al+3].[Cl-].[Cl-].[Cl-].Br[C:18]([CH3:21])([CH3:20])[CH3:19]>C(Cl)Cl>[C:18]([C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[NH:9][CH:8]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 15 °C

Procedure

To a mixture of 5-nitro-1H-indole (6.0 g, 37 mmol) and AlCl3 (24 g, 0.18 mol) in CH2Cl2 (100 mL) at 0° C. was added 2-bromo-2-methyl-propane (8.1 g, 37 mmol) dropwise. After being stirred at 15° C. overnight, the mixture was poured into ice (100 mL). The precipitated salts were removed by filtration and the aqueous layer was extracted with CH2Cl2 (30 mL×3). The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated under vacuum to obtain the crude product, which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=20:1) to give 3-tert-butyl-5-nitro-1H-indole (2.5 g, 31%). 1H NMR (CDCl3, 400 MHz) δ 8.49 (d, J=1.6 Hz, 1H), 8.31 (brs, 1H), 8.05 (dd, J=2.0, 8.8 Hz, 1H), 7.33 (d, J=8.8 Hz, 1H), 6.42 (d, J=1.6 Hz, 1H), 1.42 (s, 9H).

Workup

customThe precipitated salts were removed by filtration
extractionthe aqueous layer was extracted with CH2Cl2 (30 mL×3)
washThe combined organic layers were washed with water, brine
dry with materialdried over Na2SO4
concentrationconcentrated under vacuum
customto obtain the crude product, which
customwas purified by column chromatography on silica gel (petroleum ether/ethyl acetate=20:1)

Sources & evidence

ORD record: ord-504e71799a80444ca662ba75dbaa1d65
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08623905B2

Reaction notes

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