Azobisisobutyronitrile → HCID 66591479, compound

HRID 538421Notes

Reaction equation

HRID 538421 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH2:11][CH2:12][N:13]=2)=[CH:5][CH:4]=1.C1C(=O)N([Br:23])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:23][C:11]1[O:10][C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:14])[F:15])=[CH:8][CH:7]=2)=[N:13][CH:12]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 2725909HCID 2725909, compound

Product 1

HCID 66591479HCID 66591479, compoundYield 49.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

The above solution of 2-(4-(trifluoromethyl)phenyl)-4,5-dihydrooxazole (4.8 g, 22 mmol), NBS (11.9 g, 66.9 mmol), and AIBN (0.18 g, 1.12 mmol) in CCl4 (200 mL) was refluxed for 16 h. The resulting solution was filtered and the filtrate was washed with aqueous 10% Na2S2O3 (3×150 mL), brine (100 mL), dried (Na2SO4), and concentrated. The resulting residue was recrystallized from hexanes (350 mL) to provide 3.2 g of 5-bromo-2-(4-(trifluoromethyl)phenyl)oxazole as a crystalline solid. The filtrate and mother liquor was concentrated and purified by flash chromatography over (SiO2, 100:0-90:10 hexanes-EtOAc). to furnish an additional 1.8 g: LCMS (m/z): 294.0 (MH+), tR=1.14 min.

Workup

  1. filtrationThe resulting solution was filtered
  2. washthe filtrate was washed with aqueous 10% Na2S2O3 (3×150 mL), brine (100 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe resulting residue was recrystallized from hexanes (350 mL)

Sources & evidence

ORD record
ord-b3ad3baa9c9d4514b91b3066e87cc8bb
Source dataset
uspto-grants-2014_10
Patent number
US08865732B2

Reaction notes

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