Pyridine → 1-Acetoxy-3-fluorobenzene

HRID 277360Notes

Reaction equation

HRID 277360 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[C:15](Cl)(=[O:17])[CH3:16]>C(Cl)Cl>[C:15]([O:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 97433-Fluorophenol

Product 1

HCID 1365421-Acetoxy-3-fluorobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-fluorophenol (100 g, 0.890 mol) in methylene chloride is cooled to 0° C. to 5° C., treated with pyridine (75.0 mL, 0.930 mol), stirred for several minutes, treated dropwise with acetyl chloride (66.0 mL, 0.930 mol) while maintaining the reaction mixture temperature below 17° C., stirred at ice-bath temperature for two hours, warmed to room temperature, and poured into an ice-water mixture. The organic phase is separated, washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain the title product as a yellow oil which is identified by 1H NMR spectral analysis.

Workup

  1. temperaturewhile maintaining the reaction mixture temperature below 17° C.
  2. stirringstirred at ice-bath temperature for two hours
  3. customThe organic phase is separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-23c5babf832a465d922e8e85a0f41551
Source dataset
uspto-grants-2002_03
Patent number
US06355796B1

Reaction notes

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