Carbon Disulfide → HCID 12151613, compound

HRID 496318Notes

Reaction equation

HRID 496318 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][C:10]([Br:17])=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1.[C:18](=[S:20])=[S:19].Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>CS(C)=O>[Br:3][C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][C:10]([Br:17])=[CH:11][CH:12]=3)[C:7](=[C:18]([S:20][CH2:15][CH2:16][CH2:4][CH2:5][CH2:6][CH3:14])[S:19][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:6]=2[CH:5]=1

Participants

6

Reactant 4

HCID 6348Carbon DisulfideHCID 81011-BromohexaneHCID 24758Sodium hydrideHCID 1400732,7-Dibromofluorene

Product 1

HCID 12151613HCID 12151613, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A 60% dispersion of sodium hydride in mineral oil (0.26 g, 6.5 mmol) was added under nitrogen to 2,7-dibromofluorene (1.000 g, 3.09 mmol) in anhydrous dimethylsulfoxide (20 mL) at room temperature with stirring. The reaction mixture was stirred at room temperature for 10 minutes. Carbon disulfide (0.25 g, 0.2 mL, 3.3 mmol) was added via syringe and the reaction mixture was stirred at room temperature for 10 minutes. 1-Bromohexane (1.08 g, 6.5 mmol) was added and the reaction mixture was stirred at room temperature for 4 h. Ice-water (100 mL) was added and the resulting solid was filtered. The crude product was purified by recrystallization from iso-hexane to afford 1.225 g, (70%) as a bright yellow solid, purity 100% (GC): 1H and 13C NMR spectra as expected; M+=568 (t).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 10 minutes
  2. stirringthe reaction mixture was stirred at room temperature for 10 minutes
  3. stirringthe reaction mixture was stirred at room temperature for 4 h
  4. filtrationthe resulting solid was filtered
  5. customThe crude product was purified by recrystallization from iso-hexane
  6. customto afford 1.225 g, (70%) as a bright yellow solid, purity 100% (GC)

Sources & evidence

ORD record
ord-609627251c9b456aaa830a1a7b87daa9
Source dataset
uspto-grants-2005_09
Patent number
US06943275B2

Reaction notes

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