Phosgene → 9(+)-Fluorenylethyl chloroformate

HRID 440341Notes

Reaction equation

HRID 440341 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][CH2:15][OH:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:17](Cl)([Cl:19])=[O:18]>C1(C)C=CC=CC=1.O1CCCC1>[Cl:19][C:17]([O:16][CH2:15][CH2:14][CH:12]1[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:18]

Participants

5

Reactant 2

HCID 6371PhosgeneHCID 10921761Fluorene-9-ethanol

Product 1

HCID 149683719(+)-Fluorenylethyl chloroformate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(9-fluorenyl)ethanol 1.26 g, 6 mmol) in 10 ml of toluene and 4 ml of tetrahydrofuran (THF), was added dropwise with stirring phosgene (12.4 ml, 1.93M solution in toluene). The solution was stirred for 0.5 hours, then put under vacuum to remove the phosgene. Concentration yielded 2-(9-fluorenyl)ethyl chloroformate (6 mmol, 1.64 g).

Workup

  1. customto remove the phosgene
  2. concentrationConcentration

Sources & evidence

ORD record
ord-36f818b704fd436e8a9947a25bcadd01
Source dataset
uspto-grants-1996_05
Patent number
US05519043

Reaction notes

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