Allyl bromide → 3,6-Bis-allyloxy-5-nitrobenzo[d]isoxazole

HRID 643934Notes

Reaction equation

HRID 643934 reaction equation
[N+:1]([C:4]1[C:5]([OH:14])=[CH:6][C:7]2[O:11][N:10]=[C:9]([OH:12])[C:8]=2[CH:13]=1)([O-:3])=[O:2].[C:15](=O)([O-])[O-].[K+].[K+].[CH2:21](Br)[CH:22]=[CH2:23].CCO[C:28]([CH3:30])=O>CN(C=O)C.O>[CH2:21]([O:12][C:9]1[C:8]2[CH:13]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]([O:14][CH2:15][CH:28]=[CH2:30])=[CH:6][C:7]=2[O:11][N:10]=1)[CH:22]=[CH2:23]

Participants

7

Reactant 4

HCID 7841Allyl bromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 178526404HCID 178526404, compound

Product 1

HCID 667509873,6-Bis-allyloxy-5-nitrobenzo[d]isoxazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5-nitrobenzo[d]isoxazole-3,6-diol (1.1 g, 5.61 mmol) and potassium carbonate (3.9 g, 28.2 mmol) in DMF (10 mL) is added dropwise allyl bromide (1.42 mL, 8.30 mmol). The mixture is stirred at room temperature for 18 h. The mixture is diluted with EtOAc, and ice and water are added. The organic phase is separated and washed with water and brine, and dried over MgSO4, filtered and concentrated to afford 3,6-bis-allyloxy-5-nitrobenzo[d]isoxazole as a solid.

Workup

  1. additionare added
  2. customThe organic phase is separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2c906fd46f1a49499d32b446c10ea8d7
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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