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

HRID 1582384노트

반응식

HRID 1582384 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 227212132-Bromo-6-fluoro-3,4-dimethoxybenzonitrile수율 85%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-a90c0015477b4c4eb58cf3c9438a68a4
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734303B2

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