6-amino-3-bromo-2-fluorobenzonitrile → HCID 86662399、化合物

HRID 389465ノート

反応式

HRID 389465 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

HCID 86662399HCID 86662399、化合物収率 52%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f71bab9a48a344959e0540a7a68dbbcc
出典データセット
uspto-grants-2013_02
特許番号
US08378104B2

反応ノート

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