Fluorene → HCID 22407005, compound

HRID 440347Notes

Reaction equation

HRID 440347 reaction equation
[CH:1]1[C:13]2[CH2:12][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([Li])CCC.Br[CH2:20][CH2:21][CH2:22][C:23]#[N:24]>C1COCC1>[CH:1]1[C:13]2[CH:12]([CH2:20][CH2:21][CH2:22][C:23]#[N:24])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 6853FluoreneHCID 214124-BromobutyronitrileHCID 178418339Butyllithium

Product 1

HCID 22407005HCID 22407005, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of fluorene (5.04 g; 30.32 mmol) in THF (50 mL) was cooled to 0° C. and treated with n-butyllithium (12.13 mL of a 2.5M solution in hexanes; 30.32 mmol). After stirring the red anion mixture for 15 minutes, 4-bromobutyronitrile (4.86 g; 31.84 mmol) in 20 mL of THF was added via syringe, and the mixture was stirred overnight. It was quenched with 100 mL of saturated ammonium chloride and extracted into ethyl acetate (2×75 mL); the organic portions were washed with brine, dried and concentrated. The crude product was purified on a silica gel column, eluted with 20% ethyl acetate in hexane, to afford 4.91 g (70%) of the product as an orange oil. 1H NMR (CDCl3): δ 1.38 (m, 4H); 2.18, 2.29 (m, 2H each); 4.10 (m, 1H); 7.37 (m, 4H); 7.45 (d, 2H); 7.75 (d, 2H).

Workup

  1. stirringthe mixture was stirred overnight
  2. customIt was quenched with 100 mL of saturated ammonium chloride
  3. extractionextracted into ethyl acetate (2×75 mL)
  4. washthe organic portions were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe crude product was purified on a silica gel column
  8. washeluted with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e6bd33f19e47439f871734c48d9b371e
Source dataset
uspto-grants-1996_05
Patent number
US05519043

Reaction notes

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