1,3-Dibromopropane → HCID 22917170, compound

HRID 1376504Notes

Reaction equation

HRID 1376504 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:12])[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[Br:13][CH2:14][CH2:15][CH2:16]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:13][CH2:14][CH2:15][CH2:16][O:12][C:5]1[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 129005323-Methoxy-4-nitrophenol2×

Product 1

HCID 22917170HCID 22917170, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-methoxy-4-nitrophenol (Intermediate 18 in EP-A-494623) (2.4 g), 1,3-dibromopropane (7.5 ml) and potassium carbonate (2.2 g) in DMF (30 ml) was stirred at room temperature for 24 h. The mixture was filtered and the filtrate was evaporated to dryness. The residue was treated with water and extracted with dichloromethane. The organic extract was then washed with 5% sodium hydroxide solution and brine, dried and concentrated in vacuo to give the title compound (3.5 g) as an oil.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to dryness
  3. additionThe residue was treated with water
  4. extractionextracted with dichloromethane
  5. extractionThe organic extract
  6. washwas then washed with 5% sodium hydroxide solution and brine
  7. customdried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2d4e141b7fda4eb2a20ba6dc48cd072b
Source dataset
uspto-grants-1997_09
Patent number
US05663179

Reaction notes

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