N-bromobutanimide → HCID 68852787, compound

HRID 1821045Notes

Reaction equation

HRID 1821045 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH2:10][CH2:11][N:12]=2)=[C:4]([CH3:13])[CH:3]=1.[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([Br:14])=[CH:11][N:12]=2)=[C:4]([CH3:13])[CH:3]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 68891239HCID 68891239, compound

Product 1

HCID 68852787HCID 68852787, compoundYield 13.7%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
85 °C

Procedure

2-(4-Bromo-2-methylphenyl)-4,5-dihydro-1,3-oxazole (0.33 g, 1.38 mmol, from Step A) was dissolved in carbon tetrachloride. AIBN (0.003 g) and N-bromosuccinimide (0.18 g, 4.14 mmol) were sequentially added, the mixture was degassed with argon for 5 min and then heated at 85° C. for 24 h. The reaction was filtered, diluted with methylene chloride (200 mL) and washed with saturated sodium bisulfite (2×100 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Silica gel chromatography eluting with 3% ethyl acetate/hexanes yielded 60 mg of the desired product: 1H NMR (500 MHz, CDCl3) δ 7.83 (d, J=8.5 Hz, 1H), 7.49 (s, 1H), 7.45 (d, J=8.2 Hz, 1H), 7.16 (s, 1H), 2.67 (s, 3H).

Workup

  1. customthe mixture was degassed with argon for 5 min
  2. filtrationThe reaction was filtered
  3. additiondiluted with methylene chloride (200 mL)
  4. washwashed with saturated sodium bisulfite (2×100 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. washSilica gel chromatography eluting with 3% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-0a3117fbb8444420be427092d66a5a4b
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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