1,3-Dibromopropane → 7-Propyl-3-neopentyl-6-(3-bromopropyloxy)-1,2-benzisoxazole

HRID 2289136Notes

Reaction equation

HRID 2289136 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][C:11]([OH:16])=[C:12]([CH2:13][CH2:14][CH3:15])[C:7]=2[O:6][N:5]=1.[Br:19][CH2:20][CH2:21][CH2:22]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:18][C:2]([CH3:17])([CH3:1])[CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][C:11]([O:16][CH2:22][CH2:21][CH2:20][Br:19])=[C:12]([CH2:13][CH2:14][CH3:15])[C:7]=2[O:6][N:5]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 1358008133-Neopentyl-7-propylbenzo[d]isoxazol-6-ol

Product 1

HCID 219110397-Propyl-3-neopentyl-6-(3-bromopropyloxy)-1,2-benzisoxazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(2,2-dimethylpropyl)-6-hydroxy-7-propylbenz[4,5]isoxazole (2.000 grams; 8.090 mmol) in dry DMF (20 mL) was treated with 1,3-dibromopropane (4.29 mL; 42.263 mmol). Cesium carbonate (2.900 grams; 8.901 mmol) was added and the mixture stirred at 20° for 8 hours. The reaction mixture was partitioned between isopropyl acetate and pH 4 buffer. The organic was washed with water, then dried over magnesium sulfate. Filtration and evaporation afforded an oil which was chromatographed over silica gel, giving the title compound.

Workup

  1. customThe reaction mixture was partitioned between isopropyl acetate and pH 4 buffer
  2. washThe organic was washed with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and evaporation
  5. customafforded an oil which
  6. customwas chromatographed over silica gel

Sources & evidence

ORD record
ord-e8682f788dad40dea00c4dfc70238d6b
Source dataset
uspto-grants-2000_07
Patent number
US06090836

Reaction notes

Loading…