Water → 2-Fluorobenzoyl chloride

HRID 655008Notes

Reaction equation

HRID 655008 reaction equation
C1(NN[C:9](=[O:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[F:16])C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)[Cl:19].C1(O)C=CC=CC=1.O>C(OCC)C.CO>[Cl:19][C:9](=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[F:16]

Participants

7

Reactant 4

HCID 962WaterHCID 996PhenolHCID 24819Phosphorus pentachlorideHCID 795270HCID 795270, compound

Product 1

HCID 98082-Fluorobenzoyl chlorideYield 39.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 5.5 g of 2-fluorobenzoic acid, 2-phenylhydrazide, 6.0 g of PCl5 and 20 ml of diethyl ether was refluxed for 1 hour, under nitrogen, and then permitted to stand at ambient temperature for about 20 hours. In the following order, a solution of 5 g of phenol in 5 ml of diethyl ether, 30 ml of methanol, and sufficient water to reach the solution cloud point, were added, dropwise, to the reaction mixture. The mixture was extracted with diethyl ether and the extract washed with water, dried over anhydrous magnesium sulfate, and concentrated in vacuo to an oil. Purification of the oil by means of flash chromatography on silica gel utilizing hexane-ethyl acetate (5%) as the eluent, followed by recrystallization from hexane yielded 1.5 g of α-chloro-2-fluorobenzaldehyde, phenylhydrazone.

Workup

  1. temperaturewas refluxed for 1 hour, under nitrogen
  2. additionwere added
  3. extractionThe mixture was extracted with diethyl ether
  4. washthe extract washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo to an oil
  7. customPurification of the oil by means of flash chromatography on silica gel
  8. customfollowed by recrystallization from hexane

Sources & evidence

ORD record
ord-0378a9b9b99d40e2806fc54219dd81a0
Source dataset
uspto-grants-1992_07
Patent number
US05134236

Reaction notes

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