1,3-Dibromopropane → HCID 58332204, compound

HRID 1891404Notes

Reaction equation

HRID 1891404 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:17][CH2:18][CH2:19][CH2:20]Br>CN(C)C=O.O>[Br:17][CH2:18][CH2:19][CH2:20][O:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 178498603HCID 178498603, compound

Product 1

HCID 58332204HCID 58332204, compoundYield 25.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

A solution of methyl 3-hydroxyisoxazole-5-carboxylate (3.5 g, 24 mmol) in N,N-dimethylformamide (20 mL) was treated with potassium carbonate (6.8 g, 49 mmol) and 1,3-dibromopropane (2.5 mL, 24 mmol) was added and the mixture was stirred at 40° C. for 1 h. The reaction was diluted with water and extracted with ethyl acetate three times. The combined extracts were dried with magnesium sulfate, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (0-70% ethyl acetate/hexanes) to give the desired product (1.6 g, 25%). MF=C8H11BrNO4; LCMS calculated for C8H11BrNO4 (M+H)+: m/z=264.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate three times
  3. dry with materialThe combined extracts were dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash chromatography (0-70% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-254d5e120b744b859551d8db8db09942
Source dataset
uspto-grants-2013_08
Patent number
US08507541B2

Reaction notes

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