Phenol → 2-Phenoxybenzonitrile

HRID 63062

반응식

HRID 63062 반응식
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[O:16]([C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

6

반응물 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 678552-Fluorobenzonitrile

생성물 1

HCID 125486162-Phenoxybenzonitrile수율 93%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

To a suspension of 2-fluorobenzonitrile (10.0 g, 82.6 mmol) and phenol (7.7 g, 5.1 mmol) in DMF (80 mL) was added K2CO3 (22.8 g, 165 mmol) at rt. The reaction was stirred at 130° C. for 10 h. The reaction mixture was diluted with water, extracted with EtAOAc (100 mL×3), washed with brine (100 mL), dried (Na2SO4), and concentrated to give 15.0 g, (93%) of the title compound as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 6.85 (1H, d, J=8.4 Hz), 7.07-7.14 (3H, m), 7.22 (1H, t, J=7.2 Hz), 7.40 (2H, t, J=8.0 Hz), 7.47 (1H, td, J=2.0, 8.4 Hz), 7.65 (1H, dd, J=1.2, 8.0 Hz).

후처리

  1. extractionextracted with EtAOAc (100 mL×3)
  2. washwashed with brine (100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d04ed86b98ac428ca31ea9d6eba71a41
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447045B2

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