Thionyl Chloride → 2,5-Dichlorophenylthioacetyl chloride

HRID 3663Notes

Reaction equation

HRID 3663 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][C:10](O)=[S:11].S(Cl)([Cl:15])=O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][C:10]([Cl:15])=[S:11]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178418334HCID 178418334, compound

Product 1

HCID 217162622,5-Dichlorophenylthioacetyl chlorideYield 106.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2,5-dichlorophenylthioacetic acid (13.0 g, 54.9 mmol) in methylene chloride (55 mL) and thionyl chloride (10 mL, 137 mmol) was heated at reflux for 3 h. The reaction mixture was allowed to cool to room temperature and was concentrated in vacuo. The residue was evaporated two times from toluene to give 14 g of 2,5-dichlorophenyl-thioacetyl chloride (100% yield) as a slightly colored product which was used in the next step without purification. 1H NMR (300 MHz, CDCl3) δ4.13 (s, 2H), 7.22 (dd, J=2, 9 Hz, 1H), 7.35 (d, J=9 Hz, 1H), 7.39 (d, J=2 Hz, 1H).

Workup

  1. temperatureat reflux for 3 h
  2. concentrationwas concentrated in vacuo
  3. customThe residue was evaporated two times from toluene

Sources & evidence

ORD record
ord-6efe1ee7b8454d5381cd919bc39975fa
Source dataset
uspto-grants-1998_03
Patent number
US05734047

Reaction notes

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