Potassium Carbonate → 2-[4-(Methylsulfanyl)phenoxy]benzonitrile

HRID 987077Notes

Reaction equation

HRID 987077 reaction equation
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:10][S:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:10][S:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[C:4]#[N:5])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 140864-(Methylthio)phenolHCID 678552-Fluorobenzonitrile

Product 1

HCID 229883902-[4-(Methylsulfanyl)phenoxy]benzonitrileYield 99.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2-Fluorobenzonitrile (15.7 mL, 149 mmol) and 4-(methylsulfanyl)phenol (25 g, 178 mmol) were dissolved in DMF (500 mL) and K2CO3 (61.8 g, 447 mmol) was then added. The mixture was heated at 100° C. for 16 h under a nitrogen atmosphere. After cooling to room temperature the mixture was evaporated to dryness and then partitioned between ether (1 L) and water (2 L). The organic layer was separated, washed with 2M NaOH (500 mL), 10% (aq) K2CO3 (500 mL), dried (MgSO4) and evaporated to give a light brown solid (35.62 g, 92%); δH (CDCl3, 400 MHz) 2.50 (3H, s), 6.82 (1H, d), 7.05 (2H, d), 7.15 (1H, t), 7.30 (2H, m), 7.43 (1H, t), 7.62 (1H, d); MS m/z (TS+) 259 (MNH4+).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. customwas evaporated to dryness
  3. custompartitioned between ether (1 L) and water (2 L)
  4. customThe organic layer was separated
  5. washwashed with 2M NaOH (500 mL), 10% (aq) K2CO3 (500 mL)
  6. dry with materialdried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-5bb04bb27d8f45eb922c00a185607226
Source dataset
uspto-grants-2003_10
Patent number
US06630504B2

Reaction notes

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