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

HRID 475272ノート

反応式

HRID 475272 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 866947484-Amino-2-chloro-5-ethynylbenzonitrile収率 99.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
75 °C

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-bf8a0827f91842a2b2cfb7eed4598c5a
出典データセット
uspto-grants-2014_01
特許番号
US08637537B2

反応ノート

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