Fluorene → HCID 22223177, compound

HRID 552873Notes

Reaction equation

HRID 552873 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[CH2:16](Br)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>CS(C)=O.C(#N)C>[CH2:16]([C:12]1([CH2:12][CH2:13][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 3

HCID 6853FluoreneHCID 123691-Bromoheptane2×HCID 14798Sodium Hydroxide3×

Product 1

HCID 22223177HCID 22223177, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolvent

Procedure

0.2 mol of fluorene is dissolved in 300 ml of DMSO at 80° C. 0.01 mol of phase transfer catalyst (aliquot) is added to the solution which is stirred for a further 5 minutes. For the alkylation, 0.5 mol of 50% sodium hydroxide solution and 0.5 mol of heptyl bromide are required. The addition is effected in three stages, and commences with the addition of one third of the amount of sodium hydroxide solution used. The solution changes color to deep red and slowly becomes yellow by addition of heptyl bromide. When the solution has become yellow, the second third of sodium hydroxide solution is added, etc. The end of the reaction is checked by means of TLC on RP18 in acetonitrile.

Workup

  1. additionThe addition

Sources & evidence

ORD record
ord-a6b95fc937624ccaab043a65a9d9ca1c
Source dataset
uspto-grants-2011_05
Patent number
US07951874B2

Reaction notes

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