Hydrochloric Acid → 9-Ethyl-9H-fluorene

HRID 915495Notes

Reaction equation

HRID 915495 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH:6]1[C:18]2CC3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]=2[CH:9]=[CH:8][CH:7]=1.BrCC.Cl>C1COCC1.O>[CH2:3]([CH:2]1[C:1]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:9]1=[CH:8][CH:7]=[CH:6][CH:18]=2)[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 6853FluoreneHCID 178418339Butyllithium

Product 1

HCID 168019-Ethyl-9H-fluorene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-75 °C

Procedure

A solution of n-butyllithium (79.52 cm3, 0.2168 mol, 2.5M in hexane) was added slowly to a solution of fluorene (30.00 g, 0.1807 mol) in THF (300 cm3) at −70° C. The solution was stirred for 1 hour at −75° C. and 1-bromoethane (17.59 cm3, 0.2349 mol) was added slowly. The solution was allowed to warm to room temperature and then stirred overnight. Dilute hydrochloric acid (200 ml, 20%) was added to the reaction mixture and stirred for a further 10 minutes. Water (250 cm3) was added and the product extracted into diethyl ether (3×300 cm3). The combined organic extracts were dried (MgSO4) and the solvent removed on a rotary evaporator. The resulting oil was purified by distillation to yield a pale yellow oil (25.00 g, 71%, b.pt.—150° C. @ 1 mbar Hg).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. stirringstirred for a further 10 minutes
  4. extractionthe product extracted into diethyl ether (3×300 cm3)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. customthe solvent removed on a rotary evaporator
  7. distillationThe resulting oil was purified by distillation
  8. customto yield a pale yellow oil (25.00 g, 71%, b.pt.—150° C. @ 1 mbar Hg)

Sources & evidence

ORD record
ord-0c04deb80e3f428d9ff5b91942cccbbb
Source dataset
uspto-grants-2007_09
Patent number
US07265163B2

Reaction notes

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