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

HRID 80761

반응식

HRID 80761 반응식
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

참가 물질

7

반응물 3

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

생성물 1

HCID 866902504-Cyclopropyl-2-hydroxybenzonitrile

시약·촉매·용매 3

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)촉매HCID 1140Toluene용매HCID 86583716Ammonium chloride ethyl acetate용매

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-4c162c32089e4416946d0dfff84ac7b6
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846656B2

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