Phosgene → 9(+)-Fluorenylethyl chloroformate

HRID 2259272Notes

Reaction equation

HRID 2259272 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-b5cd0131fbb0413fb4cb54a14a750b07
Source dataset
uspto-grants-1995_12
Patent number
US05472973

Reaction notes

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