Thionyl Chloride → 9-(Chloromethyl)-9H-fluorene

HRID 2185609Notes

Reaction equation

HRID 2185609 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14]O)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:18])=O>>[CH:1]1[C:13]2[CH:12]([CH2:14][Cl:18])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 24386Thionyl Chloride2×HCID 904669H-Fluorene-9-methanol

Product 1

HCID 223415429-(Chloromethyl)-9H-fluoreneYield 70%

Procedure

The precursor for Fm—S—Ph—CO2H, 9-fluorenylmethyl chloide (Fm—Cl) was synthesized as follows. A solution of 25.0 g of 9-fluorenmethanol (127 mmol, ALDRICH® Chemical Company was refluxed with 150 ml of thionyl chloride. for 30 minutes. The excess thionyl chloride was a removed by distillation and the residue distilled at reduced pressure, then crystallized from ethanol two times to afford 19.2 g of 9-fluorenylmethyl chloride (89.4 mmol, 70%) as a pale yellow solid.

Workup

  1. customThe precursor for Fm—S—Ph—CO2H, 9-fluorenylmethyl chloide (Fm—Cl) was synthesized
  2. customa removed by distillation
  3. distillationthe residue distilled at reduced pressure
  4. customcrystallized from ethanol two times

Sources & evidence

ORD record
ord-eb77c73dc99a45b9be9945f7e8e66670
Source dataset
uspto-grants-2002_06
Patent number
US06403324B1

Reaction notes

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