Potassium Carbonate → 5-Fluoro-2-(3-methyl-benzo[d]isoxazol-6-yloxy)-benzonitrile

HRID 909176노트

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HRID 909176 반응식
[CH3:1][C:2]1[C:6]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=2[O:4][N:3]=1.F[C:13]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:14]=1[C:15]#[N:16].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O.CCOC(C)=O>[F:21][C:18]1[CH:19]=[CH:20][C:13]([O:11][C:9]2[CH:8]=[CH:7][C:6]3[C:2]([CH3:1])=[N:3][O:4][C:5]=3[CH:10]=2)=[C:14]([CH:17]=1)[C:15]#[N:16]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 1235582,5-DifluorobenzonitrileHCID 1354978903-Methyl-1,2-benzisoxazol-6-ol

생성물 1

HCID 574841185-Fluoro-2-(3-methyl-benzo[d]isoxazol-6-yloxy)-benzonitrile수율 58%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매

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온도
100 °C

실험 절차

3-Methyl-benzo[d]isoxazol-6-ol (1v) (reference for synthesis, see Indian J. Chem. Sect. B; 19:571-575 (1980)) (1.58 g, 10.6 mmol) and 2,5-difluoro-benzonitrile (2v) (1.47 g, 10.6 mmol) were combined with potassium carbonate (1.46 g. 10.6 mmol) in 15 mL of dry DMA. The reaction was heated in a 100° C. bath for 6 hours. The reaction was cooled and diluted with EtOAc (200 mL) and washed three times with water, NH4Cl, NaHCO3, and brine. The organic solution was dried over MgSO4 and concentrated. The crude residue was purified by column chromatography (silica, 70-80% CH2Cl2/hexane) to provide compound (3v) (1.65 g, 58% yield). 1H NMR (400 MHz, CDCl3) δ 7.63 (d, J=8.6 Hz, 1H), 7.44-7.41 (m, 1H), 7.33-7.26 (m, 1H), 7.10-7.06 (m, 2H), 7.03 (dd, J=8.2, 4.7 Hz, 1H), 2.59 (s, 3H); MS (ESI+) m/z 269 (M+H) detected.

후처리

  1. temperatureThe reaction was cooled
  2. washwashed three times with water, NH4Cl, NaHCO3, and brine
  3. dry with materialThe organic solution was dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude residue was purified by column chromatography (silica, 70-80% CH2Cl2/hexane)

출처 및 근거

ORD 기록
ord-8b9e0f18529f4a99912b1da47b83e81b
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017641B2

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