Tetrabutylammonium Fluoride → 4-Amino-2-chloro-5-ethynylbenzonitrile

HRID 475272노트

반응식

HRID 475272 반응식
[NH2:1][C:2]1[C:9]([C:10]#[C:11][Si](C)(C)C)=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:16])[CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[NH2:1][C:2]1[C:9]([C:10]#[CH:11])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([Cl:16])[CH:3]=1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 862227914-Amino-2-chloro-5-[(trimethylsilyl)ethynyl]benzonitrile

생성물 1

HCID 866947484-Amino-2-chloro-5-ethynylbenzonitrile수율 99.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
75 °C

실험 절차

To a solution of 238 (1.0 g, 4 mmol) in THF (100 mL) was added tetrabutylammonium fluoride (2.0 g, 7.6 mmol). The mixture was heated at 75° C. overnight then concentrated and the residue partitioned between EtOAc (500 mL) and H2O (50 mL). The organic layer was separated, washed with brine, concentrated to dryness in vacuo. The crude was purified by CombiFlash chromatography eluting with an EtOAc/petroleum ether gradient (10% to 45% EtOAc) to afford 700 mg (48%) 4-amino-2-chloro-5-ethynylbenzonitrile (240) as yellow solid: MS (ESI) m/z=177.0 [M+1]+.

후처리

  1. concentrationthen concentrated
  2. customthe residue partitioned between EtOAc (500 mL) and H2O (50 mL)
  3. customThe organic layer was separated
  4. washwashed with brine
  5. concentrationconcentrated to dryness in vacuo
  6. customThe crude was purified by CombiFlash chromatography
  7. washeluting with an EtOAc/petroleum ether gradient (10% to 45% EtOAc)

출처 및 근거

ORD 기록
ord-bf8a0827f91842a2b2cfb7eed4598c5a
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637537B2

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