Thionyl Chloride → HCID 18955940, compound

HRID 2379687Notes

Reaction equation

HRID 2379687 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH:4](O)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1.S(Cl)([Cl:19])=O>ClCCl>[Br:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH:4]([Cl:19])[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12319462HCID 12319462, compound

Product 1

HCID 18955940HCID 18955940, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The crude benzhydryl alcohol from above (31.8 g, 107 mmole) was dissolved in 150 ml of dichloromethane and 11.7 ml (1.5 equiv.) of thionyl chloride was added dropwise over ten minutes. The solution was stirred overnight at room temperature and the solvent was removed under vacuum. The crude product was redissolved in 100 ml of toluene and the solvent was again removed under vacuum in order to eliminate excess thionyl chloride, providing crude product as a dark oil. The material was purified by short path distillation (Kugelrohr apparatus, 150° C., 0.5 mm) to give 25.8 g (76%) of (2-bromophenyl)chloro(4-chlorophenyl)methane as a pale yellow oil.

Workup

  1. customthe solvent was removed under vacuum
  2. dissolutionThe crude product was redissolved in 100 ml of toluene
  3. customthe solvent was again removed under vacuum in order
  4. customproviding crude product as a dark oil
  5. distillationThe material was purified by short path distillation (Kugelrohr apparatus, 150° C., 0.5 mm)

Sources & evidence

ORD record
ord-bc45a6fe05094f3cae132e383b144839
Source dataset
uspto-grants-1994_11
Patent number
US05364843

Reaction notes

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