Carbon Tetrachloride → 2-Fluorobenzoyl chloride

HRID 359013Notes

Reaction equation

HRID 359013 reaction equation
ClC1C=CC=CC=1NN[C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(#N)C.C(Cl)(Cl)(Cl)[Cl:42]>>[Cl:42][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[F:17]

Participants

5

Reactant 4

HCID 5943Carbon TetrachlorideHCID 6342AcetonitrileHCID 11776TriphenylphosphineHCID 151170462-Fluorobenzoic acid, 2-(2-chlorophenyl)hydrazide

Product 1

HCID 98082-Fluorobenzoyl chloride

Procedure

A mixture of 5.2 g of 2-fluorobenzoic acid, 2-(2-chlorophenyl)hydrazide, 64.3 g of triphenylphosphine, 500 ml of anhydrous acetonitrile and 19.3 ml of carbon tetrachloride was stirred at ambient temperature for 16 hours, concentrated in vacuo, and extracted with diethyl ether (4×200 ml). The extract was filtered and concentrated to an oil which, was flash chromatographed on silica utilizing hexane/ethyl acetate (25%) as the eluent. Concentration of the appropriate fractions yielded 47.5 g of α-chloro-2-fluorobenzaldehyde, (2-chlorophenyl)hydrazone.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with diethyl ether (4×200 ml)
  3. filtrationThe extract was filtered
  4. concentrationconcentrated to an oil which
  5. customchromatographed on silica

Sources & evidence

ORD record
ord-9e8914f7513b441a9041d3507b0751a4
Source dataset
uspto-grants-1991_03
Patent number
US04999356

Reaction notes

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