Water → 2-Tert-butyl-4-fluoro-5-nitro-1H-indole

HRID 1403912노트

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HRID 1403912 반응식
[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([F:14])[CH:10]=[CH:9][CH:8]=2)([CH3:4])([CH3:3])[CH3:2].[N+:15]([O-])([O-:17])=[O:16].[K+].O>OS(O)(=O)=O>[C:1]([C:5]1[NH:6][C:7]2[C:12]([CH:13]=1)=[C:11]([F:14])[C:10]([N+:15]([O-:17])=[O:16])=[CH:9][CH:8]=2)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 962WaterHCID 24434Potassium NitrateHCID 591292402-tert-butyl-4-fluoro-1H-indole

생성물 1

HCID 534211832-Tert-butyl-4-fluoro-5-nitro-1H-indole수율 73%

시약·촉매·용매 1

HCID 1118Sulfuric Acid용매

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온도
-10 °C

실험 절차

To a solution of 2-tert-butyl-4-fluoro-1H-indole (2.5 g, 10 mmol) in H2SO4 (30 mL) was added KNO3 (1.3 g, 10 mmol) at 0° C. The mixture was stirred for 0.5 h at −10° C. The mixture was poured into water and extracted with EtOAc (100 mL×3). The organic layers were washed with sat. NaCl and water, dried over anhydrous Na2SO4, and evaporated under vacuum. The crude compound was purified by column chromatography on silica gel (10% EtOAc in petroleum ether) to give 2-tert-butyl-4-fluoro-5-nitro-1H-indole (900 mg, 73%). 1H NMR (400 MHz, CDCl3) δ 8.50 (br s, 1H), 7.86 (dd, J=7.6, 8.8 Hz, 1H), 7.13 (d, J=8.8 Hz, 1H), 6.52 (dd, J=0.4, 2.0 Hz, 1H), 1.40 (s, 9H).

후처리

  1. extractionextracted with EtOAc (100 mL×3)
  2. washThe organic layers were washed with sat. NaCl and water
  3. dry with materialdried over anhydrous Na2SO4
  4. customevaporated under vacuum
  5. customThe crude compound was purified by column chromatography on silica gel (10% EtOAc in petroleum ether)

출처 및 근거

ORD 기록
ord-779f6b23a8294977947ae4ed54ea341f
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912199B2

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