1,3-Dibromopropane → 4-(3-Bromopropoxy)-3-fluorobenzonitrile

HRID 2078414Notes

Reaction equation

HRID 2078414 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([F:10])[CH:4]=1)#[N:2].C([O-])([O-])=O.[K+].[K+].[Br:17][CH2:18][CH2:19][CH2:20]Br>CN(C=O)C>[Br:17][CH2:18][CH2:19][CH2:20][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[F:10]

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 27829443-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 685196304-(3-Bromopropoxy)-3-fluorobenzonitrileYield 51.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-cyano-2-fluorophenol (8.5 g, 0.0620 mol; see Preparation D(iv) above), anhydrous K2CO3 (17.14 g, 0.124 mol) and 1,3-dibromopropane (37.7 mL, 0.372 mol) in dry DMF (80 mL) was stirred at 60° C. for 3 days under a nitrogen atmosphere. The reaction mixture was filtered through Celite® and the solvent was then evaporated under reduced pressure. The residue was purified by column chromatography over silica gel, using 4% ethyl acetate in petroleum ether, as eluent, to yield 8.2 g of the sub-title compound as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered through Celite®
  2. customthe solvent was then evaporated under reduced pressure
  3. customThe residue was purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-e0addacdab904560ae93b1992950fded
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

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