1,2-Dibromoethane → 4-(2-Bromoethoxy)-3-fluorobenzonitrile

HRID 1992365Notes

Reaction equation

HRID 1992365 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].C([O-])([O-])=O.[K+].[K+].[Br:17][CH2:18][CH2:19]Br>CN(C=O)C>[Br:17][CH2:18][CH2:19][O:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 27829443-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 159788884-(2-Bromoethoxy)-3-fluorobenzonitrileYield 60.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3-fluoro-4-hydroxybenzonitrile (20 g, 0.1459 mol, from step (iv) above), anhydrous. K2CO3 (40.33 g, 0.2918 mol) and 1,2-dibromo ethane (76.8 ml, 0.8754 mol) in dry DMF (150 ml) was stirred at 60° C. for 5 days under nitrogen atmosphere. The reaction mixture wasfiltered through celite and solvent evaporated under reduced pressure. The residue was purified by column chromatography over silica gel using 2% ethyl acetate in petroleum ether, as eluent to yield the sub-title compound (21.6 g) as a solid.

Workup

  1. customevaporated under reduced pressure
  2. customThe residue was purified by column chromatography over silica gel using 2% ethyl acetate in petroleum ether, as eluent

Sources & evidence

ORD record
ord-794e0591be994b0aae21d383bdfbed3f
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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