N-bromobutanimide → HCID 67814058, compound

HRID 589099Notes

Reaction equation

HRID 589099 reaction equation
[C:1]([O:9][CH2:10][C:11]1[O:15][N:14]=[C:13]([CH3:16])[CH:12]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>C(O)(=O)C.[Cl-].[Na+].O>[C:1]([O:9][CH2:10][C:11]1[O:15][N:14]=[C:13]([CH3:16])[C:12]=1[Br:17])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 67814333HCID 67814333, compound

Product 1

HCID 67814058HCID 67814058, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

A solution of (3-methylisoxazol-5-yl)methyl benzoate (20.1 g, 92.4 mmol) in acetic acid (77.3 mL) was treated with N-bromosuccinimide (19.7 g, 111 mmol) and heated in a sealed tube at 90° C. for 4 h. The reaction mixture was diluted with brine and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered, and concentrated to give the crude product. Purification by flash column chromatography (100% hexanes to 20% ethyl acetate/hexanes) gave the desired product (21.6 g, 79%). LCMS calculated for C12H11BrNO3 (M+H)+: m/z=296.0, 298.0. found: 296.0, 298.0.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product
  8. customPurification by flash column chromatography (100% hexanes to 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-b669b41331534a05928d8d454468e18b
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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