t-Butyl bromide → HCID 44622906, 화합물

HRID 468331노트

반응식

HRID 468331 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 31.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
15 °C

실험 절차

To a mixture of 5-nitro-1H-indole (6 g, 36.8 mmol) and AlCl3 (24 g, 0.18 mol) in CH2Cl2 (100 mL) was added 2-bromo-2-methyl-propane (8.1 g, 36.8 mmol) dropwise at 0° C. After being stirred at 15° C. overnight, the reaction 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-00d3ed7afc7349af88b99f93631928b8
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623905B2

반응 노트

불러오는 중…