Thionyl Chloride → 1-[Chloro(phenyl)methyl]-4-fluorobenzene

HRID 2202605Notes

Reaction equation

HRID 2202605 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)O)=[CH:4][CH:3]=1.S(Cl)([Cl:18])=O>ClCCl>[Cl:18][CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 5707534-Fluorobenzhydrol

Product 1

HCID 2162561-[Chloro(phenyl)methyl]-4-fluorobenzeneYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (30 mL), (±)-(4-fluorophenyl)phenylmethanol (2.1 g, 10 mmol) synthesized in Production Example 195 was dissolved, and thionyl chloride (5.1 g, 42 mmol) was added dropwise thereto at a room temperature. After the completion of the dropping, the mixture was heated under reflux, and the completion of the reaction was confirmed by TLC. After the completion of the reaction, the reaction mixture was concentrated, diluted with ethyl acetate, and washed with water. The organic layer was dried over magnesium sulfate, and the solvent was distilled off. Thus the title compound (2.1 g, 94%) was obtained.

Workup

  1. dissolutionwas dissolved
  2. customat a room temperature
  3. temperatureAfter the completion of the dropping, the mixture was heated
  4. temperatureunder reflux
  5. customAfter the completion of the reaction
  6. concentrationthe reaction mixture was concentrated
  7. additiondiluted with ethyl acetate
  8. washwashed with water
  9. dry with materialThe organic layer was dried over magnesium sulfate
  10. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-5873cc4dd1494309bcc9ab90319b79c8
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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