7-Bromo-2-(4-hydroxyphenyl)-1,3-benzoxazol-5-ol → HCID 135430308, compound

HRID 1824787Notes

Reaction equation

HRID 1824787 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=[C:4]([OH:18])[CH:3]=1.[C:19]([Cu])#[N:20]>CN(C=O)C.C(OCC)(=O)C>[OH:18][C:4]1[CH:3]=[C:2]([C:19]#[N:20])[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 1354183737-Bromo-2-(4-hydroxyphenyl)-1,3-benzoxazol-5-olHCID 178418546HCID 178418546, compound

Product 1

HCID 135430308HCID 135430308, compoundYield 25.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

To 7-bromo-2-(4-hydroxy-phenyl)-benzooxazol-5-ol (96 mg) in DMF (3 mL) was added CuCN (84 mg). The mixture was placed in an oil bath and heated to 150° C. for 3 h. The mixture was cooled to room temperature and diluted with ethyl acetate and washed with 1N HCl, saturated aqueous EDTA, brine (3×), dried (Na2SO4), and concentrated. Flash chromatography on silica gel eluting with 20% ethyl acetate-hexane afforded 20 mg (25%) of the title compound as a solid. MS: 253 (MH+), HPLC tR: 2.06 min.

Workup

  1. customThe mixture was placed in an oil bath
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with 1N HCl, saturated aqueous EDTA, brine (3×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-eace9916bb6647bbaf688be63e02a76f
Source dataset
uspto-grants-2006_05
Patent number
US07045539B2

Reaction notes

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