Benzyl Bromide → 4-(Benzyloxy)-2-fluorobenzonitrile

HRID 1815948Notes

Reaction equation

HRID 1815948 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(=O)([O-])[O-].[K+].[K+].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CC(C)=O>[CH2:17]([O:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27346752-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 113336284-(Benzyloxy)-2-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-fluoro-4-hydroxybenzonitrile (15.0 g, 109 mmol), potassium carbonate (21.0 g, 152 mmol), and benzyl bromide (19.6 g, 115 mmol) in acetone (150 mL) under nitrogen was heated at 50° C. overnight. The solid was removed by filtration and the filtrate evaporated to a residue that was mixed with ethyl acetate (500 mL). This solution was washed with brine, dried, and evaporated to give an amorphous solid: (24.9 g, 100%).

Workup

  1. customThe solid was removed by filtration
  2. customthe filtrate evaporated to a residue that
  3. additionwas mixed with ethyl acetate (500 mL)
  4. washThis solution was washed with brine
  5. customdried
  6. customevaporated
  7. customto give an amorphous solid

Sources & evidence

ORD record
ord-6dc1315e4eaf4d598b2284bdd80f843f
Source dataset
uspto-grants-2005_04
Patent number
US06881749B2

Reaction notes

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