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

HRID 1715598ノート

反応式

HRID 1715598 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bf6eb57fc41347e0a64b241c538e841b
出典データセット
uspto-grants-2010_09
特許番号
US07799782B2

反応ノート

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