1,3-Dibromopropane → HCID 68581877, compound

HRID 645420Notes

Reaction equation

HRID 645420 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][C:10]([Br:17])=[CH:11][CH:12]=3)[CH2:7][C:6]=2[CH:5]=1.Br[CH2:19][CH2:20][CH2:21]Br>CS(C)=O.O>[Br:3][C:4]1[CH:16]=[CH:15][C:14]2[C:13]3[C:8](=[CH:9][C:10]([Br:17])=[CH:11][CH:12]=3)[C:7]3([CH2:21][CH2:20][CH2:19]3)[C:6]=2[CH:5]=1

Participants

6

Reactant 3

HCID 80011,3-DibromopropaneHCID 14797Potassium HydroxideHCID 1400732,7-Dibromofluorene

Product 1

HCID 68581877HCID 68581877, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Powdered KOH (983 mg, 17.5 mmol) was added in batches over 1 minute to a heterogeneous mixture of 2,7-dibromo-9H-fluorene (1.31 g, 4.04 mmol) and 1,3-dibromopropane (837 mg, 4.15 mmol) in DMSO (20 mL), and stirred at ambient condition for ˜5 days. The mixture was diluted with water (200 mL) and extracted with 10% CH2Cl2/hexanes (100 mL, 2×). The combined organic phase was dried (MgSO4), filtered, and concentrated in vacuo. The resulting crude material was purified with a column chromatography (sample was loaded as a silica gel mesh; hexanes, with gravity elution) to afford 2′,7′-dibromospiro[cyclobutane-1,9′-fluorene] as a white fluffy solid (600 mg). 1H NMR (CDCl3, δ=7.24, 400 MHz): 7.86 (d, J=1.8, 2H), 7.48 (d, J=8.0, 2H), 7.44 (dd, J=8.1, 1.8, 2H), 2.61 (app t, J=8.1, 4H), 2.42-2.34 (m, 2H).

Workup

  1. extractionextracted with 10% CH2Cl2/hexanes (100 mL, 2×)
  2. dry with materialThe combined organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude material was purified with a column chromatography (sample
  6. washhexanes, with gravity elution)

Sources & evidence

ORD record
ord-6151c2e4884048569282e8a8264807e1
Source dataset
uspto-grants-2010_04
Patent number
US07704992B2

Reaction notes

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