1,3-Dibromopropane → HCID 10988726, compound

HRID 1992391Notes

Reaction equation

HRID 1992391 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].[Br:10][CH2:11][CH2:12][CH2:13]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:10][CH2:11][CH2:12][CH2:13][O:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 759273,4-Difluorophenol

Product 1

HCID 10988726HCID 10988726, compoundYield 86.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 3,4-difluorophenol (2.60 g, 20.0 mmol), 1,3-dibromopropane (20.3 mL, 2001 mmol), and potassium carbonate (2.76 g, 20.0 mmol) in acetonitril (30 mL) was heated at 75° C. overnight. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The crude product was purified by chromatography on silica gel. (Horizon™, flash system from Biotage™. Column: Flash 40+M, 40×150 mm. Eluent: 3% ethyl acetate in heptane. Concentration in vacuo afforded, 4.35 g of the title compound as a colourless oil with a purity of ca. 90%.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe crude product was purified by chromatography on silica gel
  4. concentrationConcentration in vacuo
  5. customafforded

Sources & evidence

ORD record
ord-da6bbe135740427682fafa0757c9fef2
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

Loading…