Water → 3-Bromo-2-fluoro-5-nitrobenzonitrile

HRID 389466노트

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HRID 389466 반응식
N[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]([Br:13])=[C:6]([F:14])[C:3]=1[C:4]#[N:5].N(OC(C)(C)C)=O.O>O1CCCC1>[Br:13][C:7]1[C:6]([F:14])=[C:3]([CH:2]=[C:9]([N+:10]([O-:12])=[O:11])[CH:8]=1)[C:4]#[N:5]

참가 물질

5

반응물 3

HCID 962WaterHCID 10906Tert-Butyl nitriteHCID 86662399HCID 86662399, 화합물

생성물 1

HCID 667600553-Bromo-2-fluoro-5-nitrobenzonitrile수율 53%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

To a cooled (0° C.) solution of 2-amino-5-bromo-6-fluoro-3-nitro-benzonitrile (8.0 g, 30.8 mmol) in tetrahydrofuran (40 mL) was added tert-butyl nitrite (4.6 mL, 37 mmol) dropwise and stirred for 16 h at 50° C. The reaction mixture was treated with water and extracted with ethyl acetate. The organic fraction was washed with water and brine, dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography (2% to 10% ethyl acetate:hexanes) afforded 4.0 g (53%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 8.72 (dd, J=3.0, 2.7 Hz, 1H), 8.51 (dd, J=3.0, 2.7 Hz, 1H).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic fraction was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography (2% to 10% ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-1939ce7545e848309d9de087f932eb13
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08378104B2

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