Hydrochloric Acid → HCID 66642757、化合物

HRID 1171010ノート

反応式

HRID 1171010 の反応式
C([O:9][C:10]1[CH:15]=[C:14](I)[C:13]([O:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([CH:26]([CH3:28])[CH3:27])[CH:19]=2)=[C:12](I)[CH:11]=1)(=O)C1C=CC=CC=1.[C:30]([Cu])#[N:31].Cl.[CH3:34][N:35](C=O)C>>[C:34]([C:14]1[CH:15]=[C:10]([OH:9])[CH:11]=[C:12]([C:30]#[N:31])[C:13]=1[O:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([CH:26]([CH3:27])[CH3:28])[CH:19]=1)#[N:35]

参加物

5

反応物 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 25150328HCID 25150328、化合物HCID 178418546HCID 178418546、化合物

生成物 1

HCID 66642757HCID 66642757、化合物

反応条件

温度
160 °C

実験手順

To a stirred solution of 3,5-diiodo-4-(4′-methoxy-3′-iso-propylphenoxy)phenyl benzoate (0.4 g, 0.76 mmol) in DMF(5.0 mL) at rt was added CuCN (0.27 g, 3.0 mmol). The reaction mixture was heated at 160° C. for 5 min under microwave irradiation, the reaction mixture was cool to room temperature and poured into 1N HCl (50 mL) and extracted with ethyl acetate (100 mL×2). The organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate-hexanes (3:7) to afford 3,5-dicyano-4-(4′-methoxy-3′-iso-propylphenoxy)phenol as a viscous (105 mg, 35%): 1H NMR (300 MD, CDCl3): δ 7.35 (s, 2 H), 6.99 (d, J=3.0 Hz, 1 H), 6.78 (d, J=8.7 Hz, 1 H), 6.99 (dd, J=3.0, 8.7 Hz, 1 H), 3.84 (s, 3 H), 3.38-3.30 (m, 1 H), 1.21 (d, J=6.9 Hz, 6 H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=hexanes-ethyl acetate (7:3); Rf=0.38.

後処理

  1. temperaturethe reaction mixture was cool to room temperature
  2. extractionextracted with ethyl acetate (100 mL×2)
  3. dry with materialThe organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with ethyl acetate-hexanes (3:7)

出典と根拠

ORDレコード
ord-ddd2a87df691435199e9a01b0b5fd997
出典データセット
uspto-grants-2010_11
特許番号
US07829552B2

反応ノート

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