1,3-Dibromopropane → 1-(3-Bromopropoxy)-2-fluorobenzene

HRID 1992389Notes

Reaction equation

HRID 1992389 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[Br:9][CH2:10][CH2:11][CH2:12]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:9][CH2:10][CH2:11][CH2:12][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 97072-FluorophenolHCID 11430Potassium Carbonate

Product 1

HCID 71722931-(3-Bromopropoxy)-2-fluorobenzeneYield 100.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-fluorophenol (2.24 g, 20.0 mmol), 1,3-dibromopropane (20.3 mL, 200 mmol), and potassium carbonate (2.76 g, 20.0 mmol) in acetonitril (30 mL) was heated at 80° C. overnight. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give 4.70 g of the title compound as a light yellow oil with a purity of ca. 80%. The product was used in the subsequent reaction step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fac461edfc9d4ba1ad4af5a58bd9295a
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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