6-amino-3-bromo-2-fluorobenzonitrile → HCID 86662399, 화합물

HRID 389465노트

반응식

HRID 389465 반응식
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([F:10])[C:5]([Br:11])=[CH:4][CH:3]=1.F[B-](F)(F)F.[O:17]=[N+:18]=[O:19]>C(#N)C.[Cl-].[Na+].O>[NH2:1][C:2]1[C:3]([N+:18]([O-:19])=[O:17])=[CH:4][C:5]([Br:11])=[C:6]([F:10])[C:7]=1[C:8]#[N:9]

참가 물질

5

반응물 2

HCID 27611996-amino-3-bromo-2-fluorobenzonitrileHCID 11073463Nitronium tetrafluoroborate

생성물 1

HCID 86662399HCID 86662399, 화합물수율 52%

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 57417360Sodium chloride; water용매

실험 절차

To a cooled (0° C.) solution of 6-amino-3-bromo-2-fluoro-benzonitrile (8.0 g, 37 mmol) in acetonitrile (40 mL) under nitrogen was added dropwise a solution of nitronium tetrafluoroborate in acetonitrile. The reaction mixture and stirred for 16 h at RT. The reaction mixture was treated with brine and extracted with ethyl acetate. The organic fraction was washed with water followed by brine and dried over anhydrous sodium sulfate, filtered and concentrated. Purification by column chromatography (10 to 20% ethyl acetate:hexanes) afforded 5.0 g (52%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 8.6 (d, J=6.9 Hz, 1H), 6.8-7.1 (br. s, 2H).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic fraction was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography (10 to 20% ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-f71bab9a48a344959e0540a7a68dbbcc
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08378104B2

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