1,10-Phenanthroline → 2-(4-Bromophenyl)benzo(d)oxazole

HRID 1912159Notes

Reaction equation

HRID 1912159 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Br[C:12]1[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=1[NH2:14].C([O-])([O-])=O.[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>O1CCOCC1.[Cu]I>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[O:7][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 119922-BromoanilineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 128467152-(4-Bromophenyl)benzo(d)oxazoleYield 87%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 4-bromobenzoylchloride (4.84 g, 22 mmol), 2-bromoaniline (3.8 g, 22 mmol), CuI (0.21 g, 1.1 mmol), Cs2CO3 (14.3 g, 44 mmol) and 1,10-phenathroline (0.398 g, 2.2 mmol) in anhydrous 1,4-dioxane (80 mL) was degassed and heated at about 125° C. under argon overnight. The mixture was cooled and poured into ethyl acetate (˜200 mL) and filtered. The filtrate was absorbed on silica gel, purified by column chromatography (hexanes/ethyl acetate 4:1), and precipitated by hexanes to give a white solid (5.2 g, in 87% yield).

Workup

  1. customwas degassed
  2. temperatureThe mixture was cooled
  3. additionpoured into ethyl acetate (˜200 mL)
  4. filtrationfiltered
  5. customThe filtrate was absorbed on silica gel
  6. custompurified by column chromatography (hexanes/ethyl acetate 4:1)
  7. customprecipitated by hexanes
  8. customto give a white solid (5.2 g, in 87% yield)

Sources & evidence

ORD record
ord-1c79b292ba4544d9b9f76e3f4e5cd753
Source dataset
uspto-grants-2013_12
Patent number
US08604689B2

Reaction notes

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