Water → 1,2-Bis(fluorenyl)ethane

HRID 841120

Reaction equation

HRID 841120 reaction equation
Br[CH2:2][C:3]1[C:15]2[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.O>C1COCC1>[C:3]1([CH2:2][CH2:2][C:3]2[C:15]3[CH2:14][C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:7]=3[CH:6]=[CH:5][CH:4]=2)[C:15]2[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 962WaterHCID 259258(Bromo)(fluorenyl)methane

Product 1

HCID 178250291,2-Bis(fluorenyl)ethane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5.1 g, 19.6 mmol 1-bromomethylfluorene dissolved in 50 ml THF was added dropwise to 0.24 g, 9.9 mmol Mg in 10 ml THF. After addition the Grignard was refluxed for 2 hrs, cooled and water/aqueaous HCl added. After work-up this afforded 1.5 g of CH2CH2(1-fluorenyl)2 as a beige powder. 1H NMR (CDCl3): δ 3.81 ppm (CH2), 3.14 ppm (CH2).

Workup

  1. additionAfter addition the Grignard
  2. temperaturewas refluxed for 2 hrs
  3. temperaturecooled

Sources & evidence

ORD record
ord-2d6978fdcae64e9aad4031a1a25bf1f7
Source dataset
uspto-grants-2002_04
Patent number
US06369254B1

Linked notes

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