Ethyl Bromide → 9-Ethyl-1,2,3,4-tetrahydrofluorene

HRID 1256864Notes

Reaction equation

HRID 1256864 reaction equation
[CH2:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH2:3][CH2:2]1.[CH2:14]([Li])[CH2:15]CC.C(Br)C>C1COCC1.CCCCCC>[CH2:14]([CH:12]1[C:13]2[CH2:1][CH2:2][CH2:3][CH2:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:15]

Participants

6

Reactant 3

HCID 6332Ethyl BromideHCID 5884652,3,4,9-Tetrahydro-1H-fluoreneHCID 178418339Butyllithium

Product 1

HCID 177831249-Ethyl-1,2,3,4-tetrahydrofluoreneYield 75%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

5.3 g (31.1 mmol) of the above-obtained 1,2,3,4-tetrahydrofluorene was placed in a 500 mL four-neck flask, to which 100 mL of THF was added under a nitrogen atmosphere. 10 mL (2.6 mol/L) of a hexane solution of n-butyllithium was slowly added dropwise to the solution under stirring at −78° C., followed by stirring at room temperature for 2 hours. 0.89 g (8.2 mmol) of ethyl bromide was added thereto at 0° C. over 2 minutes, followed by stirring at room temperature for 4 hours. After completing the reaction, THF was removed to provide 3.4 g of 9-ethyl-1,2,3,4-tetrahydrofluorene (9-Et-4HFluH) as a colorless oily matter (yield: 75%).

Workup

  1. additionwas added under a nitrogen atmosphere
  2. stirringby stirring at room temperature for 2 hours
  3. stirringby stirring at room temperature for 4 hours
  4. customwas removed

Sources & evidence

ORD record
ord-e827e74dea28493b835c0210674b78d6
Source dataset
uspto-grants-2013_06
Patent number
US08461270B2

Reaction notes

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