Hydrochloric Acid → 4-Acetyl-2-fluorobenzonitrile

HRID 411650

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HRID 411650 반응식
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1.C1C=CC(P(C2C=CC=[CH:38][CH:39]=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N#N.Cl.CN(C=[O:47])C>CC([O-])=O.CC([O-])=O.[Pd+2].O>[C:38]([C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1)(=[O:47])[CH3:39]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 6228DimethylformamideHCID 812191,3-Bis(diphenylphosphino)propaneHCID 7360294-Bromo-2-fluorobenzonitrile

생성물 1

HCID 224816534-Acetyl-2-fluorobenzonitrile

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 962Water용매

반응 조건

온도
90 °C

실험 절차

A mixture of 5.0 g (0.02 mol) 4-bromo-2-fluorobenzonitrile, 6 ml TEA, 906 mg (0.0022 mol) dppp, 5.8 g (0.04 mol) TIOAc, and 448 mg (0.002 mol) Pd(OAc)2 in 50 ml DMF was deaired under a stream of N2 The mixture was heated to 90° C. for 7 hours. The reaction was cooled to room temperature and 25 mL 2N HCl was added and stirred to 30 minutes. The mixture was poured into 300 ml water and extracted with Et2O (2×300 mL). The combined organics were washed with water (2×80 mL), brine (1×80 mL), dried over MgSO4 and concentrated to give an oil, which was then chromatographed on silica gel eluted with 30% ethyl acetate/70% hexanes to give 2.5 g of a yellow/orange oil.

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. extractionextracted with Et2O (2×300 mL)
  3. washThe combined organics were washed with water (2×80 mL), brine (1×80 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give an oil, which
  7. customwas then chromatographed on silica gel
  8. washeluted with 30% ethyl acetate/70% hexanes

출처 및 근거

ORD 기록
ord-b274483724dd4b3e94d791cd1b8a9e69
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06559168B2

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