Methyl iodide → 9,9-Dimethylfluorene

HRID 2273378Notes

Reaction equation

HRID 2273378 reaction equation
[CH:1]1[C:13]2CC3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:14][C:15]([CH3:18])([O-])[CH3:16].[K+].IC>CS(C)=O>[CH3:14][C:15]1([CH3:18])[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:16]1=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 6853FluoreneHCID 23665647Potassium tert-butoxide

Product 1

HCID 783259,9-DimethylfluoreneYield 81.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
10 °C

Procedure

A 2000 mL round flask was charged with 9H-fluorene (50 g, 300.1 mmol) and potassium t-butoxide (77.0 g, 721.9 mmol), and then 700 mL of DMSO was slowly injected thereto. Under nitrogen atmosphere, iodomethane (113.5 g, 800 mmol) was slowly dropped through a dropping funnel while the reactor temperature was maintained at 10° C. or lower. The mixture was stirred at room temperature for 24 hours, and the reaction was terminated by addition of 500 mL of distilled water. The organic layer collected by extraction with n-hexane was dried over magnesium sulfate, followed by removal of volatile materials, and then purified with n-hexane by using silica gel column chromatography tube, followed by drying, to thereby obtain 47.5 g of 9,9-dimethyl-9H-fluorene (yield: 81.50%) as white solid.

Workup

  1. customthe reaction was terminated by addition of 500 mL of distilled water
  2. customThe organic layer collected by extraction with n-hexane
  3. dry with materialwas dried over magnesium sulfate
  4. customfollowed by removal of volatile materials
  5. custompurified with n-hexane
  6. customby drying

Sources & evidence

ORD record
ord-079368a5c07849628feb891aec3aa29c
Source dataset
uspto-grants-2015_09
Patent number
US09120884B2

Reaction notes

Loading…