N-Fluorobenzenesulfonimide → HCID 66914960, compound

HRID 880457Notes

Reaction equation

HRID 880457 reaction equation
C([Li])CCC.Br[C:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][N:9]([CH3:18])[C:8]=1[CH3:19].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:30])(=O)=O)=CC=1>O1CCCC1>[F:30][C:7]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][N:9]([CH3:18])[C:8]=1[CH3:19]

Participants

5

Reactant 3

HCID 588007N-FluorobenzenesulfonimideHCID 66914773HCID 66914773, compoundHCID 178418339Butyllithium

Product 1

HCID 66914960HCID 66914960, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

n-Butyllithium (2.06 mL, 1.6M solution, 3.30 mmol) was added to a solution of 3-bromo-1,2-dimethyl-4-phenyl-pyrrole (550 mg, 2.20 mmol) in tetrahydrofuran (10 mL) at −78° C. and the reaction mixture was stirred at −78° C. for 30 min. A solution of n-fluorodibenzene sulfonamide (901 mg, 2.86 mmol) in tetrahydrofuran (8 mL) was added to the reaction mixture at −78° C. and the reaction mixture was stirred at this temperature for another 1 h. The reaction mixture was allowed to warm to ambient temperature and stirred for 16 h after which time the reaction mixture was quenched with dilute HCl and evaporated to dryness. The residue was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product. Purification by preparative HPLC afforded 3-fluoro-1,2-dimethyl-4-phenyl-pyrrole (160 mg, 39%) as a solid.

Workup

  1. stirringthe reaction mixture was stirred at this temperature for another 1 h
  2. temperatureto warm to ambient temperature
  3. stirringstirred for 16 h after which time the reaction mixture
  4. customwas quenched with dilute HCl
  5. customevaporated to dryness
  6. additionThe residue was diluted with water
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with water, brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customto give the crude product
  12. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-187537e9c570449280774ad70e02995a
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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