Hydrochloric Acid → HCID 66642757, 화합물

HRID 1171010노트

반응식

HRID 1171010 반응식
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]

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 25150328HCID 25150328, 화합물HCID 178418546HCID 178418546, 화합물

생성물 1

HCID 66642757HCID 66642757, 화합물

반응 조건

온도
160 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ddd2a87df691435199e9a01b0b5fd997
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829552B2

반응 노트

불러오는 중…