Dichloromethane → 4-(Benzyloxy)-2-fluorobenzonitrile

HRID 1456360Notes

Reaction equation

HRID 1456360 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].ClCCl>C(#N)C>[F:15][C:16]1[CH:23]=[C:22]([O:24][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:21]=[CH:20][C:17]=1[C:18]#[N:19]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 27346752-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 113336284-(Benzyloxy)-2-fluorobenzonitrileYield 84.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

15.2 ml (0.127 mol) of benzyl bromide and 29.3 g (0.212 mol) of potassium carbonate are added to a solution of 13.3 g (0.106 mol) of 2-fluoro-4-hydroxybenzonitrile in 150 ml of acetonitrile. The mixture is stirred at reflux for 1 hour 30 minutes and then filtered, the filtrate is concentrated under reduced pressure, and the oil obtained is diluted in the minimum amount of dichloromethane. After crystallization by addition of diisopropyl ether, filtration and drying, 20.3 g of product are obtained. Melting point : 87° C.

Workup

  1. temperatureat reflux for 1 hour 30 minutes
  2. filtrationfiltered
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customthe oil obtained
  5. customAfter crystallization
  6. additionby addition of diisopropyl ether, filtration
  7. customdrying

Sources & evidence

ORD record
ord-896ec0e06715400fa274248c5d1f7a22
Source dataset
uspto-grants-1998_12
Patent number
US05843975

Reaction notes

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