Water → 2-Fluorobenzoyl chloride

HRID 359016Notes

Reaction equation

HRID 359016 reaction equation
FC1C=CC(NN[C:10](=[O:18])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=CC=1.P(Cl)(Cl)(Cl)(Cl)[Cl:20].C1(O)C=CC=CC=1.O>C(OCC)C.CO>[Cl:20][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17]

Participants

7

Reactant 4

HCID 962WaterHCID 996PhenolHCID 24819Phosphorus pentachlorideHCID 14370937HCID 14370937, compound

Product 1

HCID 98082-Fluorobenzoyl chlorideYield 121.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred mixture of 79.5 g of 2-fluorobenzoic acid, 2-(4-fluorophenyl)hydrazide in 350 ml of diethyl ether was added, portionwise, 80.0 g of phosphorous pentachloride. Upon completion of the addition, the reaction mixture was refluxed for 1 hr and then stirred at ambient temperature for 16 hrs. In the following order, a solution of 81.3 g of phenol in 80 ml of diethyl ether, 385 ml of methanol, and sufficient water to reach the solution cloud point, were added, dropwise, to the reaction mixture. Upon standing the reaction mixture separated into two layers. The bottom layer was collected, washed with water, and extracted with diethyl ether. The extract was washed with water, dried over anhydrous magnesium sulfate and concentrated to an oil. The oil was purified by flash chromatography on silica gel using 5% ethyl acetate-hexane as the eluent. Evaporation of the appropriate fractions gave 61.5 g of α-chloro-2-fluorobenzaldehyde, (4-fluorophenyl)hydrazone as an oil. Distillation gave the analytical sample bp 144°-155°.

Workup

  1. additionwas added
  2. additionUpon completion of the addition
  3. temperaturethe reaction mixture was refluxed for 1 hr
  4. additionwere added
  5. customseparated into two layers
  6. customThe bottom layer was collected
  7. washwashed with water
  8. extractionextracted with diethyl ether
  9. washThe extract was washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated to an oil
  12. customThe oil was purified by flash chromatography on silica gel using 5% ethyl acetate-hexane as the eluent
  13. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-b02f035c14784f4295e4cc3eb18d2429
Source dataset
uspto-grants-1991_03
Patent number
US04999356

Reaction notes

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