t-Butyl bromide → HCID 44622906、化合物

HRID 468312ノート

反応式

HRID 468312 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 44622906HCID 44622906、化合物収率 31%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
15 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-504e71799a80444ca662ba75dbaa1d65
出典データセット
uspto-grants-2014_01
特許番号
US08623905B2

反応ノート

読み込み中…