1,2-Dibromoethane → 4-(2-Bromoethoxy)-3,5-difluorobenzonitrile

HRID 2078406Notes

Reaction equation

HRID 2078406 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1[OH:10])[C:5]#[N:6].C([O-])([O-])=O.[K+].[K+].[Br:18][CH2:19][CH2:20]Br>CN(C=O)C>[Br:18][CH2:19][CH2:20][O:10][C:9]1[C:2]([F:1])=[CH:3][C:4]([C:5]#[N:6])=[CH:7][C:8]=1[F:11]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 107494063,5-Difluoro-4-hydroxy-benzonitrile

Product 1

HCID 691364604-(2-Bromoethoxy)-3,5-difluorobenzonitrileYield 70.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 3,5-difluoro-4-hydroxybenzonitrile (10 g, 0.0649 mol; see Preparation B(iv) above), anhydrous K2CO3 (17.94 g, 0.1298 mol) and 1,2-dibromoethane (73.2 g, 0.389 mol) in dry DMF (100 mL) was stirred at 60° C. overnight 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 1.5% ethyl acetate in petroleum ether as eluent, to yield 12 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-2fdcf606919f4c3799e102f1f98f90ca
Source dataset
uspto-grants-2011_04
Patent number
US07928225B2

Reaction notes

Loading…