1,2-Dibromoethane → Bis(tetrahydrofluorenyl)ethane

HRID 1279901Notes

Reaction equation

HRID 1279901 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][CH2:16][CH3:17].Br[CH2:20][CH2:21]Br.[NH4+].[Cl-]>C1COCC1.CCCCCC>[CH:10]1([CH:16]([CH:15]2[C:14]3[CH2:21][C:20]4[C:3](=[CH:2][CH:1]=[CH:13][CH:12]=4)[C:4]=3[CH2:5][CH2:6][CH2:7]2)[CH3:17])[C:11]2[CH2:12][C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH2:7][CH2:8][CH2:9]1

Participants

7

Reactant 4

HCID 78391,2-DibromoethaneHCID 25517Ammonium ChlorideHCID 5884652,3,4,9-Tetrahydro-1H-fluoreneHCID 178418339Butyllithium

Product 1

HCID 86758507Bis(tetrahydrofluorenyl)ethane

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

Tetrahydrofluorene (17.6 mmol) was dissolved in 20 ml of dry THF and cooled to 0° C. Butyllithium, (11 ml of a solution 1.6M in hexane, 17.6 mmol) was added dropwise to give a red/orange solution that was stirred for 6h. 1,2-dibromoethane (1.66 g, 8.81 mmol) was added quickly. The resulting beige suspension was stirred overnight. The mixture was hydrolyzed with NH4Cl and extracted in THF and diethyl ether. The organics were collected, dried, filtered and the solvents were removed to give a yellow solid.

Workup

  1. customto give a red/orange solution that
  2. stirringThe resulting beige suspension was stirred overnight
  3. extractionextracted in THF
  4. customThe organics were collected
  5. customdried
  6. filtrationfiltered
  7. customthe solvents were removed
  8. customto give a yellow solid

Sources & evidence

ORD record
ord-9d47347e8eb440a2aa9344df04847779
Source dataset
uspto-grants-2002_09
Patent number
US06448424B1

Reaction notes

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