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

HRID 389466ノート

反応式

HRID 389466 の反応式
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]

参加物

5

反応物 3

HCID 962WaterHCID 10906Tert-Butyl nitriteHCID 86662399HCID 86662399、化合物

生成物 1

HCID 667600553-Bromo-2-fluoro-5-nitrobenzonitrile収率 53%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1939ce7545e848309d9de087f932eb13
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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