Methyl iodide → 2,7-Dibromo-9-(bis-methylsulfanyl-methylene)fluorene

HRID 496317Notes

Reaction equation

HRID 496317 reaction equation
CC(C)([O-])C.[Na+].[Br:7][C:8]1[CH:20]=[CH:19][C:18]2[C:17]3[C:12](=[CH:13][C:14]([Br:21])=[CH:15][CH:16]=3)[CH2:11][C:10]=2[CH:9]=1.[C:22](=S)([S:25][CH3:26])[S:23][CH3:24].CI>CS(C)=O>[Br:7][C:8]1[CH:20]=[CH:19][C:18]2[C:17]3[C:12](=[CH:13][C:14]([Br:21])=[CH:15][CH:16]=3)[C:11](=[C:22]([S:25][CH3:26])[S:23][CH3:24])[C:10]=2[CH:9]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 16840Dimethyl trithiocarbonateHCID 1400732,7-DibromofluoreneHCID 23676156Sodium t-butoxide

Product 1

HCID 121516122,7-Dibromo-9-(bis-methylsulfanyl-methylene)fluorene

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium tert-butoxide (1.24 g, 12.9 mmol) was added portionwise over 2 min to a solution of 2,7-dibromofluorene (2.0 g, 6.2 mmol) in DMSO (40 ml) at RT under nitrogen. To the resulting red solution was added dimethyl trithiocarbonate (0.94 g, 6.8 mmol) via a syringe. The reaction was stirred for 5 min and methyl iodide (1.8 g, 12.6 mmol) was added over 2 min. The reaction was stirred for 1 h worked up as above. Recrystallization from ethyl acetate/THF (2:1) afforded 2.4 g (91%). The sample was identical in all respects to that described above.

Workup

  1. stirringThe reaction was stirred for 1 h
  2. customRecrystallization from ethyl acetate/THF (2:1)
  3. customafforded 2.4 g (91%)

Sources & evidence

ORD record
ord-33e6120b4b1d4b3ab12ced330b3b47e2
Source dataset
uspto-grants-2005_09
Patent number
US06943275B2

Reaction notes

Loading…