4-Bromophenol → 4-(4-Bromophenoxy)benzonitrile

HRID 1483615Notes

Reaction equation

HRID 1483615 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([O:17][C:14]2[CH:15]=[CH:16][C:11]([Br:10])=[CH:12][CH:13]=2)=[CH:3][CH:4]=1)#[N:7]

Participants

5

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 145174-Fluorobenzonitrile

Product 1

HCID 223473964-(4-Bromophenoxy)benzonitrileYield 87.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Under nitrogen, the mixture of 4-fluorobenzonitrile (7.35 g, 60.68 mmol), 4-bromophenol (10 g, 57.8 mmol) and potassium carbonate (12 g, 1.5 eq) in DMF (100 mL) was stirred at 100° C. for 16 h and then filtered. After rotary evaporation, the residue was dissolved in ethyl acetate and washed with 1N NaOH solution to remove unreacted phenol. The organic solution was dried and passed through a short silica gel column to remove the color and minor phenol impurity. Evaporation of the solution gave (4-cyanophenyl)(4-bromophenyl)ether (13.82 g, yield 87.2%) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 7.83 (d, 2H), 7.63 (d, 2H), 7.13 (d, 2H) and 7.10 (d, 2H) ppm.

Workup

  1. filtrationfiltered
  2. customAfter rotary evaporation
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with 1N NaOH solution
  5. customto remove unreacted phenol
  6. customThe organic solution was dried
  7. customto remove the color and minor phenol impurity
  8. customEvaporation of the solution

Sources & evidence

ORD record
ord-755d40f58afb457085d40c993463e7ec
Source dataset
uspto-grants-2016_08
Patent number
US09416146B2

Reaction notes

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