Potassium Phosphate, Tribasic → 4-Cyclopropyl-2-hydroxybenzonitrile

HRID 80761

反応式

HRID 80761 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([OH:10])[CH:3]=1.[CH:11]1([B-](F)(F)F)[CH2:13][CH2:12]1.[K+].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CCOC(C)=O.[NH4+].[Cl-].CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[CH:11]1([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([OH:10])[CH:3]=2)[CH2:13][CH2:12]1

参加物

7

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 129669614-Bromo-2-hydroxybenzonitrileHCID 23697338Potassium cyclopropyltrifluoroborate

生成物 1

HCID 866902504-Cyclopropyl-2-hydroxybenzonitrile

試薬・触媒・溶媒 3

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)触媒HCID 1140Toluene溶媒HCID 86583716Ammonium chloride ethyl acetate溶媒

反応条件

温度
100 °C

実験手順

A solution of 4-bromo-2-hydroxybenzonitrile (1 g, 5.05 mmol), potassium cyclopropyltrifluoroborate (1.495 g, 10.10 mmol), K3PO4 (5.05 ml, 15.15 mmol) and PdCl2(Amphos)2 (0.358 g, 0.505 mmol) in toluene (25 mL) was allowed to stir at 100° C. under nitrogen overnight. The mixture was then cooled to room temperature, diluted with EtOAc/NH4Cl(aq), and filtered through a pad of Celite. The organic layer was seperated, dried over Na2SO4, filtered and concentrated. The residue was purified by FCC (0-50% EtOAc/heptane) to provide 4-cyclopropyl-2-hydroxybenzonitrile, 1H NMR (400 MHz, CH2Cl2) δ 12.17 (br. s., 1H), 7.23 (d, J=8.34 Hz, 1H), 6.51-6.58 (m, 2H), 1.82 (tt, J=5.02, 8.37 Hz, 1H), 0.94-1.00 (m, 2H), 0.68-0.73 (m, 2H).

後処理

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationfiltered through a pad of Celite
  3. customThe organic layer was seperated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by FCC (0-50% EtOAc/heptane)

出典と根拠

ORDレコード
ord-4c162c32089e4416946d0dfff84ac7b6
出典データセット
uspto-grants-2014_09
特許番号
US08846656B2

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