Tetrabutylammonium Fluoride → 2-Bromo-6-fluoro-3,4-dimethoxybenzonitrile

HRID 1582384ノート

反応式

HRID 1582384 の反応式
[F-:1].C([N+](CCCC)(CCCC)CCCC)CCC.[Br:19][C:20]1[C:27]([O:28][CH3:29])=[C:26]([O:30][CH3:31])[CH:25]=[C:24]([N+]([O-])=O)[C:21]=1[C:22]#[N:23]>C(OCC)(=O)C>[Br:19][C:20]1[C:27]([O:28][CH3:29])=[C:26]([O:30][CH3:31])[CH:25]=[C:24]([F:1])[C:21]=1[C:22]#[N:23]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 227212172-Bromo-3,4-dimethoxy-6-nitrobenzonitrile

生成物 1

HCID 227212132-Bromo-6-fluoro-3,4-dimethoxybenzonitrile収率 85%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

A partially dried solution of tetrabutylammonium flouride (24 ml, 1M in THF stored over 4A sieves) was added to 2-bromo-3,4-dimethoxy-6-nitrobenzonitrile (prepared according to step (c), 1.73 g, 6.02 mmol) with stirring at room temperature. After 1 hour ethyl acetate was added and the mixture washed with 1M aqueous HCl (50 ml). The aqueous wash was extracted with ethyl acetate (50 ml) and the combined organics then washed with aqueous NaHCO3 (50 ml) before being dried over MgSO4 and concentrated in vacuo. The crude residue was recrystallised from toluene:tert-butylmethylether (1:1) to give 1.34 g of the subtitle product (85%).

後処理

  1. washthe mixture washed with 1M aqueous HCl (50 ml)
  2. washThe aqueous wash
  3. extractionwas extracted with ethyl acetate (50 ml)
  4. washthe combined organics then washed with aqueous NaHCO3 (50 ml)
  5. dry with materialbefore being dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was recrystallised from toluene:tert-butylmethylether (1:1)

出典と根拠

ORDレコード
ord-a90c0015477b4c4eb58cf3c9438a68a4
出典データセット
uspto-grants-2004_05
特許番号
US06734303B2

反応ノート

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