Dimethylformamide → 3-(Benzyloxy)-5-(2-chlorophenoxy)-2-nitropyridine

HRID 1426165노트

반응식

HRID 1426165 반응식
[CH2:1]([O:8][C:9]1[C:10]([N+:16]([O-:18])=[O:17])=[N:11][CH:12]=[C:13](Cl)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[OH:32].CN(C=O)C>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[C:10]([N+:16]([O-:18])=[O:17])=[N:11][CH:12]=[C:13]([O:32][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[Cl:25])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 72452-ChlorophenolHCID 11430Potassium CarbonateHCID 673694373-(Benzyloxy)-5-chloro-2-nitropyridine

생성물 1

HCID 673694033-(Benzyloxy)-5-(2-chlorophenoxy)-2-nitropyridine수율 54.2%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

A mixture of 3-(benzyloxy)-5-chloro-2-nitropyridine (1.00 g, 3.78 mmol), potassium carbonate (2.09 g, 15.1 mmol), 2-chlorophenol (1.46 g, 11.3 mmol) and DMF (16 mL) was heated at 100° C. for 2 hours. The reaction mixture was cooled, partitioned between a 1:1 mixture of ethyl acetate (60 mL) and ether and water (60 mL). The organic layer was washed with 2N NaOH (30 mL), water, and brine, dried, and concentrated. The residue was purified by MPLC (Biotage) eluting with 5:1 hexane:ethyl acetate to afford 3-(benzyloxy)-5-(2-chlorophenoxy)-2-nitropyridine (0.73 g, 54.2% yield) as a light yellow solid. 1H NMR (CDCl3) δ 5.16 (s, 2H), 6.90 (s, 1H), 7.09 (d, 1H), 7.28-7.37 (m, 7H), 7.52 (d, 1H), 7.72 (s, 1H).

후처리

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between a 1:1 mixture of ethyl acetate (60 mL) and ether and water (60 mL)
  3. washThe organic layer was washed with 2N NaOH (30 mL), water, and brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by MPLC (Biotage)
  7. washeluting with 5:1 hexane

출처 및 근거

ORD 기록
ord-27019af157bc4f0d8690ad89af05e1d3
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933077B2

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