N-Fluorobenzenesulfonimide → 1-Fluoroanthracene

HRID 2260845Notes

Reaction equation

HRID 2260845 reaction equation
C([Li])CCC.Br[C:7]1[C:20]2[C:11](=[CH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=[CH:9][CH:8]=1.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:31])(=O)=O)=CC=1>C(OCC)C.O1CCCC1>[F:31][C:7]1[C:20]2[C:11](=[CH:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 588007N-FluorobenzenesulfonimideHCID 125298271-BromoanthraceneHCID 178418339Butyllithium

Product 1

HCID 130686551-FluoroanthraceneYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1.2 millimoles n-butyl lithium were dropped into a solution of 1 millimole bromoanthracene in 5 milliliters diethyl ether at 5° C. The solution was cooled to 0° C., was stirred for 1 hour, and then was cooled further to -78° C.; 1.2 millimoles N-fluorobenzenesulfonimide prepared according to Example 1 above in 5 milliliters tetrahydrofuran were dropped into the mixture which was stirred for 1 hour. The temperature was allowed to rise to 20° C. while stirring was continued. The reaction mixture was quenched by pouring into saturated ammonium chloride solution and extracted with diethyl ether. Fluoroanthracene was obtained in 76% yield.

Workup

  1. temperaturewas cooled further to -78° C.
  2. additionwere dropped into the mixture which
  3. stirringwas stirred for 1 hour
  4. customto rise to 20° C.
  5. stirringwhile stirring
  6. customThe reaction mixture was quenched
  7. additionby pouring into saturated ammonium chloride solution
  8. extractionextracted with diethyl ether

Sources & evidence

ORD record
ord-944d7f9977f641f8aa558b544aaeee0b
Source dataset
uspto-grants-1995_12
Patent number
US05478964

Reaction notes

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