HCID 53821226、化合物 → Methyl 3-cyano-4-isobutylbenzoate

HRID 2189755ノート

反応式

HRID 2189755 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1OS(C(F)(F)F)(=O)=O)[C:6]([O:8][CH3:9])=[O:7])#[N:2].Br[Zn][CH2:23][CH:24]([CH3:26])[CH3:25]>O1CCCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:23][CH:24]([CH3:26])[CH3:25])[C:6]([O:8][CH3:9])=[O:7])#[N:2]

参加物

4

反応物 2

HCID 53821226HCID 53821226、化合物HCID 178448255HCID 178448255、化合物

生成物 1

HCID 59316752Methyl 3-cyano-4-isobutylbenzoate収率 22.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To methyl 3-cyano-4-{[(trifluoromethyl)sulfonyl]oxy}benzoate (D19) (1.5 g, 4.85 mmol) was added bromo(2-methylpropyl)zinc (48.5 ml, 24.25 mmol) in tetrahydrofuran (50 ml) under argon. To the solution was then added 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium(II) dichloromethane complex (0.355 g, 0.485 mmol) and the reaction heated to reflux for 6 h. The mixture was quenched with water (2 mL) and then filtered through celite, washing with ethyl acetate. The solvent was removed in vacuo. The residue was partitioned between ethyl acetate (50 mL) and water (50 mL) and the organic phase dried (phase separator) and the solvent removed in vacuo. The residue was purified by silica chromatography, eluting 0-15% EtOAc in iso-hexane over 40 min. Two batches were collected, one of which was the title compound as a colourless oil (233 mg, 1.072 mmol). δH (CDCl3, 400 MHz): 8.28 (1H, d), 8.15 (1H, dd), 7.38 (1H, d), 3.94, 3H, s), 2.78 (2H, d), 2.02 (1H, m), 0.96 (6H, d).

後処理

  1. temperatureadded 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium(II) dichloromethane complex (0.355 g, 0.485 mmol) and the reaction heated
  2. temperatureto reflux for 6 h
  3. customThe mixture was quenched with water (2 mL)
  4. filtrationfiltered through celite
  5. washwashing with ethyl acetate
  6. customThe solvent was removed in vacuo
  7. customThe residue was partitioned between ethyl acetate (50 mL) and water (50 mL)
  8. customthe organic phase dried (phase separator)
  9. customthe solvent removed in vacuo
  10. customThe residue was purified by silica chromatography
  11. washeluting 0-15% EtOAc in iso-hexane over 40 min
  12. customTwo batches were collected

出典と根拠

ORDレコード
ord-1f7016f53e5045ac9e8d167110efc084
出典データセット
uspto-grants-2012_12
特許番号
US08324254B2

反応ノート

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