9-Bromofluorene → Methyl [(9H-fluoren-9-yl)sulfanyl]acetate

HRID 1898951Notes

Reaction equation

HRID 1898951 reaction equation
[H-].[Na+].[C:3]([O:7][CH3:8])(=[O:6])[CH2:4][SH:5].Br[CH:10]1[C:22]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2>O1CCCC1>[CH:12]1[C:11]2[CH:10]([S:5][CH2:4][C:3]([O:7][CH3:8])=[O:6])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]=2[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 160249-BromofluoreneHCID 16907Methyl ThioglycolateHCID 24758Sodium hydride

Product 1

HCID 14114712Methyl [(9H-fluoren-9-yl)sulfanyl]acetateYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (840 mg of 60% NaH in oil, 21.0 mmol) in 40 mL of tetrahydrofuran is added methyl thioglycolate (1.68 mL, 18.8 mmol). The mixture is stirred at room temperature for 20 minutes. 9-Bromofluorene (Aldrich) (5.23 g, 21.3 mmol) in 30 mL of tetrahydrofuran is added and the reaction mixture is stirred at room temperature overnight then concentrated to dryness. The residue is taken up in ethyl acetate and washed with brine, saturated aqueous sodium bicarbonate, and again with brine. The organic layer is dried over magnesium sulfate, concentrated in vacuo and chromatographed on silica gel, eluting with 10% ethyl acetate in hexane to provide 908 mg (18%) of methyl (9-fluorenylthio)acetate as a colorless oil.

Workup

  1. stirringthe reaction mixture is stirred at room temperature overnight
  2. concentrationthen concentrated to dryness
  3. washwashed with brine, saturated aqueous sodium bicarbonate
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customchromatographed on silica gel
  7. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-16cd1034cfa64e3d8739fd9031842094
Source dataset
uspto-grants-1996_11
Patent number
US05571825

Reaction notes

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