Ethyl Acetate → HCID 135409725, compound

HRID 858250Notes

Reaction equation

HRID 858250 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[O-].[Na+].[C:22](OCC)(=[O:24])C>CN(C)C=O.Cl.[Cu]Br>[OH:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[O:9][C:10]3[C:2]([O:24][CH3:22])=[CH:3][C:4]([OH:18])=[CH:5][C:6]=3[N:7]=2)=[CH:12][CH:13]=1

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 1354183737-Bromo-2-(4-hydroxyphenyl)-1,3-benzoxazol-5-ol

Product 1

HCID 135409725HCID 135409725, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 24593copper(I) bromideCatalystHCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 7-bromo-2-(4-hydroxyphenyl)-1,3-benzoxazol-5-ol (100 mg, 0.33 mmol), and copper(I) bromide (56 mg, 0.39 mmol) in anhydrous N,N dimethylformamide (1.5 mL) was stirred with freshly prepared sodium methoxide (15 wt % in methanol, 1 ml) and heated to 120° C. for 4 h. The mixture was cooled and diluted with HCl (1N, 5 ml). Isolation of the crude product with ethyl acetate followed by flash chromatography (40%–50% EtOAc/petroleum ether) gave the title compound as an off-white solid (50 mg, 60% yield, mp 225–228° C.); MS m/e 258 (M+H)+.

Workup

  1. temperatureThe mixture was cooled

Sources & evidence

ORD record
ord-9ea45b4985a84d8d82e3ca94ce923077
Source dataset
uspto-grants-2006_12
Patent number
US07148247B2

Reaction notes

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