t-Butyl bromide → HCID 44622906, 화합물

HRID 503305노트

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HRID 503305 반응식
[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]

참가 물질

5

반응물 3

HCID 10485t-Butyl bromideHCID 225235-NitroindoleHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 44622906HCID 44622906, 화합물수율 31%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
15 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-03749259290b4848aed87c858b9b5060
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07776905B2

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