Guaiacol → HCID 118006083, compound

HRID 1049616Notes

Reaction equation

HRID 1049616 reaction equation
F[C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([I:11])[CH:3]=1.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[I:11][C:4]1[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([O:20][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 460GuaiacolHCID 11430Potassium CarbonateHCID 2590861-Fluoro-3-iodo-5-nitrobenzene

Product 1

HCID 118006083HCID 118006083, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-fluoro-3-iodo-5-nitrobenzene (5.0 g, 18.0 mmol), 2-methoxyphenol (2.3 g, 18.0 mmol) in dry DMSO (10.0 mL) and anhydrous K2CO3 (3.8 g, 27.5 mmol) was heated at 110° C. for 16 h. The mixture was poured into ice water and extracted with EtOAc (3×50 mL). The organic layer was sequentially washed with brine (2×75 mL), dried over anhydrous Na2SO4, concentrated by rotary evaporation, and purified by column chromatography to give 1-iodo-3-(2-methoxyphenoxy)-5-nitrobenzene (7) (4.7g, 70%). 1H NMR (400 MHz, CDCl3) δ 8.23-8.13 (m, 1H), 7.69-7.48 (m, 2H), 7.30-7.25 (m, 1H), 7.12-6.93 (m, 3H), 3.80 (d, J=1.9 Hz, 3H).

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe organic layer was sequentially washed with brine (2×75 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated by rotary evaporation
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-65a83706eead44819d2f630fe8b4a16a
Source dataset
uspto-grants-2016_07
Patent number
US09382245B2

Reaction notes

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