Thionyl Chloride → (4-Fluorophenoxy)acetyl chloride

HRID 1731240Notes

Reaction equation

HRID 1731240 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8](O)=[O:9])=[CH:4][CH:3]=1.S(Cl)([Cl:15])=O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([Cl:15])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 678824-Fluorophenoxyacetic acid

Product 1

HCID 2759057(4-Fluorophenoxy)acetyl chlorideYield 95.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a 100 ml round bottom flask equipped with a magnetic stirrer, reflux condenser equipped with a connector to a 50% sodium hydroxide trap, 6.81 g (0.040 mole) para-fluorophenoxyacetic acid (the product of Example 2), 2.96 ml (0.044 mole) thionyl chloride, and about 40 ml toluene were placed. The reaction mixture was stirred at reflux for two hours, allowed to cool to room temperature, and then concentrated to give 7.2 g of the product, a brown liquid.

Workup

  1. customInto a 100 ml round bottom flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. customequipped with a connector to a 50% sodium hydroxide trap
  4. temperatureat reflux for two hours
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c4a19c64a5af48beb842d9ca06c2a2e8
Source dataset
uspto-grants-1986_11
Patent number
US04620867

Reaction notes

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