Sodium hydride → HCID 25270922, compound

HRID 2421808Notes

Reaction equation

HRID 2421808 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[H-].[Na+].S(O[CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38])(C1C=CC(C)=CC=1)(=O)=O>C1COCC1>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38])([CH2:29][CH2:30][O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:37][CH3:38])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1400732,7-DibromofluoreneHCID 99488982-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate

Product 1

HCID 25270922HCID 25270922, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2,7-dibromofluorene (5.0 g, 15.4 mmol) was dissolved in dried THF solution (30 mL). Sodium hydride (1.0 g, 40 mmol) was added to the THF solution at room temperature and refluxed for 5 hours. 1-Tosyloxy-3,6,9-trioxadecane (11.8 g, 37 mmol) in 20 mL of dry THF was added drop-wise to the refluxed solution. The mixture was allowed to refluxed over night, then cooled down, poured into distill water and extracted with chloroform (2×100 mL). The combined organic solutions were washed with saturated NaCI solution (2×100 mL), distilled water (1×100 mL), dried over MgSO4, and concentrated under reduced pressure. Crude oil was further purified by column chromatography using hexane/ethyl acetate (50/50) as eluant. TLC (ethyl acetate/Hexane=1/1) Rf =0.12. The fraction at Rf=0.12 was collected and concentrated to give 5.7 product in 60% yield. 1H NMR (300 MHz, CDCl3), 2.34(t, 4H), 2.77(t, 4H), 3.10-3.60(m, 22H), 7.40-7.60(m, 6H).

Workup

  1. temperaturerefluxed for 5 hours
  2. temperatureto refluxed over night
  3. temperaturecooled down
  4. additionpoured
  5. distillationinto distill water
  6. extractionextracted with chloroform (2×100 mL)
  7. washThe combined organic solutions were washed with saturated NaCI solution (2×100 mL)
  8. distillationdistilled water (1×100 mL)
  9. dry with materialdried over MgSO4
  10. concentrationconcentrated under reduced pressure
  11. customCrude oil was further purified by column chromatography
  12. customThe fraction at Rf=0.12 was collected
  13. concentrationconcentrated
  14. customto give 5.7 product in 60% yield

Sources & evidence

ORD record
ord-c8ba514b21434f569a71d2286ba2c342
Source dataset
uspto-grants-2011_06
Patent number
US07960037B2

Reaction notes

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