N-bromobutanimide → HCID 23157338, compound

HRID 2110860Notes

Reaction equation

HRID 2110860 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:8]([O:10][CH3:11])=[O:9])([CH3:3])[CH3:2].[Br:16]N1C(=O)CCC1=O>C(OCC)(=O)C.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:16][CH2:15][C:14]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[O:4][CH:1]([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 23157412Methyl 3-isopropoxy-4-methylbenzoate

Product 1

HCID 23157338HCID 23157338, compoundYield 64.6%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-isopropoxy-4-methylbenzoate (1.0 g, 4.8 mmol) in ethyl acetate (20 mL) were added N-bromosuccinimide (0.92 g, 5.19 mmol) and 2,2′-azobis(isobutyronitrile) (3 mg), and the mixture was heated under reflux for 6 hr. The reaction mixture was cooled, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=4/1) to give the title compound (0.89 g, yield 64%) as a colorless oil. MS (ESI+): 287 (M+H), 289.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hr
  3. temperatureThe reaction mixture was cooled
  4. washwashed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-8d3f1d5bad4d4079bd133a38260a098a
Source dataset
uspto-grants-2009_04
Patent number
US07517910B2

Reaction notes

Loading…