Water → HCID 58473621, compound

HRID 1254960Notes

Reaction equation

HRID 1254960 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)[CH:5]([CH3:16])[C:4]=2[CH:3]=1.[OH-].[K+].O.Br[CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35]>CS(C)=O.ClCCl>[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]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]3[C:29](=[O:30])[C:28]4[C:27](=[CH:34][CH:33]=[CH:32][CH:31]=4)[C:26]3=[O:35])([CH3:16])[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 93575N-(4-Bromobutyl)phthalimideHCID 125898062,7-Dibromo-9-methyl-9H-fluorene

Product 1

HCID 58473621HCID 58473621, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

2,7-dibromo-9-methyl-9H-fluorene (10.0 g, 29.58 mmol) was dissolved in 50 mL DMSO under nitrogen. To mixture was added KOH (2.01 g, 35.79 mmol), water (1.5 mL), N-(4-bromobutyl)phthalimide (9.93 g, 35.2 mmol), and stirred reaction at room temperature for 2.0 hours, then at 50° C. for 3.0 hours. The reaction was cooled to room temperature and diluted with dichloromethane. The organic layer was washed with brine (2×), and water. Removal of solvent yield a solid, which was purified by column chromatography (7:3, hexanes:EtOAc) to yield white solids (3.08 g, 20%). 1H NMR (500 MHz, CDCl3): δ=7.81-7.83 (m, 2H), 7.68-7.71 (m, 2H), 7.48-7.51 (m, 4H), 7.41-7.44 (dd, 2H), 3.46-3.49 (t, 2H), 2.00-2.04 (p, 2H), 1.47-1.49 (m, 2H), 1.45 (s, 3H), 0.65-0.68 (m, 2H).

Workup

  1. customreaction at room temperature for 2.0 hours
  2. washThe organic layer was washed with brine (2×), and water
  3. customRemoval of solvent
  4. customyield a solid, which
  5. customwas purified by column chromatography (7:3, hexanes:EtOAc)

Sources & evidence

ORD record
ord-d4dbce21cc1942d89aaa59f8f7df84a7
Source dataset
uspto-grants-2013_06
Patent number
US08455613B2

Reaction notes

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