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

HRID 2121864Notes

Reaction equation

HRID 2121864 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:15][C:16]1[CH:23]=[C:22]([OH:24])[CH:21]=[CH:20][C:17]=1[C:18]#[N:19]>CC(C)=O>[CH2:1]([O:24][C:22]1[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[C:16]([F:15])[CH:23]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

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

Product 1

HCID 113336284-(Benzyloxy)-2-fluorobenzonitrileYield 97%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

Benzyl bromide (467 mL, 3.93 mol) and potassium carbonate (1.4 kg, 10.1 mol) were added to a solution of 2-fluoro-4-hydroxybenzonitrile (490 g, 3.57 mol) in acetone (3.4 L). The stirred mixture was heated at 60° C. for 20 h, then cooled and filtered. The filtrate was concentrated and the resulting solid was triturated with 10% ethyl acetate-hexane (5 L) and vacuum dried at 35° C. to give the desired product (787 g, 97%).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe resulting solid was triturated with 10% ethyl acetate-hexane (5 L) and vacuum
  5. customdried at 35° C.

Sources & evidence

ORD record
ord-37f80420ba284428b8b80925e82b713f
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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