Carbon Tetrachloride → 2-Fluorobenzoyl chloride

HRID 359029Notes

Reaction equation

HRID 359029 reaction equation
FC1C=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 151170492-Fluorobenzoic acid, 2-(2-fluorophenyl)hydrazide

Product 1

HCID 98082-Fluorobenzoyl chloride

Procedure

To a stirred mixture, under nitrogen, of 3.0 g of 2-fluorobenzoic acid, 2-(2-fluorophenyl)hydrazide, 3.0 g of triphenylphosphine, and 25 ml of acetonitrile was added, dropwise, 1.6 g of carbon tetrachloride. The reaction mixture was stirred for 22 hours at ambient temperature and concentrated to an oil. Flash chromatography on silica gel, eluting with 25% ethyl acetate/hexane afforded α-chloro-2-fluorobenzaldehyde, (2-fluorophenyl)hydrazone as an oil.

Workup

  1. concentrationconcentrated to an oil
  2. washFlash chromatography on silica gel, eluting with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-516f50f4309746e69ccaf34f5f100463
Source dataset
uspto-grants-1991_03
Patent number
US04999356

Reaction notes

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