Hydrochloric Acid → HCID 66642757, compound

HRID 2108650Notes

Reaction equation

HRID 2108650 reaction equation
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]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 25150328HCID 25150328, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 66642757HCID 66642757, compoundYield 35%

Conditions

Temperature
160 °C

Procedure

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 oil (105 mg, 35%): 1H NMR (300 MHz, 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.

Workup

  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)

Sources & evidence

ORD record
ord-e8d1bb447eaf4a12b414c49963fe25a6
Source dataset
uspto-grants-2009_04
Patent number
US07514419B2

Reaction notes

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