Hydrochloric Acid → HCID 21107101, compound

HRID 1765396Notes

Reaction equation

HRID 1765396 reaction equation
Br[C:2]1[C:7]2[C:8](=[O:20])[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[CH:10][O:11][C:6]=2[CH:5]=[C:4]([O:21][CH3:22])[CH:3]=1.[I-:23].[K+].Cl>CS(C)=O.[Cu]I>[I:23][C:2]1[C:7]2[C:8](=[O:20])[C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[CH:10][O:11][C:6]=2[CH:5]=[C:4]([O:21][CH3:22])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 21107090HCID 21107090, compound

Product 1

HCID 21107101HCID 21107101, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
115 °C

Procedure

A suspension of 5-bromo-7-methoxy-3-(4-methoxyphenyl)-4-oxo-4H-1-benzopyran (95 mg), copper(I) iodide (250 mg) and potassium iodide (462 mg) in DMSO (6 mL) was heated at 115° C. for 2 h. The mixture was cooled, poured into 1M hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with 1M hydrochloric acid and brine and dried over MgSO4. Chromatography on silica gel (eluant: ethyl acetate-dichloromethane-hexane 1:10:20) afforded the title compound (95 mg). 1H NMR (DMSO-d6): 8.40 (s, 1H), 7.63 (d, 1H, J=2.7 Hz), 7.47 (d, 2H, J=8.7 Hz), 7.22 (d, 1H, J=2.7 Hz), 6.99 (d, 2H, J=8.7 Hz), 3.90 (s, 3H), 3.79 (s, 3H); MS: 409 (MH+); HPLC tR: 2.83 min.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with 1M hydrochloric acid and brine
  4. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-8d802a4500fd426ab489364b4becf9ca
Source dataset
uspto-grants-2007_06
Patent number
US07226945B2

Reaction notes

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