Dimethylformamide → 2-(1-Chloroethyl)-9H-fluorene

HRID 2393500Notes

Reaction equation

HRID 2393500 reaction equation
S(Cl)([Cl:3])=O.CN(C)C=O.O[CH:11]([C:13]1[CH:25]=[CH:24][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][C:15]=2[CH:14]=1)[CH3:12]>C(Cl)Cl>[Cl:3][CH:11]([C:13]1[CH:25]=[CH:24][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][C:15]=2[CH:14]=1)[CH3:12]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 26584520371-86-2

Product 1

HCID 145724842-(1-Chloroethyl)-9H-fluorene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (1.1 ml) and catalytically effective amount of N,N-dimethylformamide were added to a solution of 2-(1-hydroxyethyl)-9H-fluorene (1.05 g) in methylene chloride (15 ml) under ice-cooling, and the mixture was stirred at room temperature for 30 minutes and then heated under reflux for 1 hour. By evaporating the solvent under reduced pressure, 2-(1-chloroethyl)-9H-fluorene was obtained.

Workup

  1. temperaturecooling
  2. temperatureheated
  3. temperatureunder reflux for 1 hour
  4. customBy evaporating the solvent under reduced pressure

Sources & evidence

ORD record
ord-07ed4ea18b1a4fd9b1ae585a97fa8fbf
Source dataset
uspto-grants-1998_09
Patent number
US05807880

Reaction notes

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