Potassium Carbonate → 3-Fluoro-4-(3-hydroxypropoxy)-benzonitrile

HRID 1992379Notes

Reaction equation

HRID 1992379 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[C:5]([F:10])[CH:4]=1)#[N:2].Br[CH2:12][CH2:13][CH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:10][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[O:9][CH2:12][CH2:13][CH2:14][OH:15])[C:1]#[N:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 27829443-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 436575093-Fluoro-4-(3-hydroxypropoxy)-benzonitrileYield 77.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-cyano-2-fluoro phenol (5 g, 0.0365 mol; from prep N(iv) above), 3-bromopropanol (10.15 g, 0.073 mol) and potassium carbonate (7.6 g, 0.054 mol) in dry acetone (50 ml) was stirred at 60° C. overnight under nitrogen atmosphere. The reaction mixture was filtered and the solvent was concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using 5% ethyl acetate in petroleum ether to yield (5.5 g) of the sub-title compound as a solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe solvent was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography over silica gel using 5% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-b5ec3a9f9231402581764b3a1b9898f8
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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