Acetic Acid → HCID 67814058, compound

HRID 2401333Notes

Reaction equation

HRID 2401333 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.CC(O)=O.C1C(=O)N([Br:28])C(=O)C1>O>[C:1]([O:9][CH2:10][C:11]1[O:15][N:14]=[C:13]([CH3:16])[C:12]=1[Br:28])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 67814333HCID 67814333, compound

Product 1

HCID 67814058HCID 67814058, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

To a resealable vial was added (3-methylisoxazol-5-yl)methyl benzoate (907 mg, 4.18 mmol), AcOH (3.5 mL, 61.1 mmol), and NBS (892 mg, 5.01 mmol). The reaction was heated to 110° C. overnight. The reaction was cooled to room temperature and diluted with water. The aqueous was extracted with EtOAc and the combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford (4-bromo-3-methylisoxazol-5-yl)methyl benzoate. LC/MS m/z 296 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionThe aqueous was extracted with EtOAc
  3. washthe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified via Biotage (EtOAc/hex)

Sources & evidence

ORD record
ord-4e9eef0047fc45878dfe1f867c203117
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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