1-Bromonaphthalene → 1-Cyclopropylnaphthalene

HRID 885588Notes

Reaction equation

HRID 885588 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.Br[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][CH:8]=1>O1CCCC1.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[CH:1]1([C:15]2[C:16]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 70011-BromonaphthaleneHCID 178418630HCID 178418630, compound

Product 1

HCID 146686931-CyclopropylnaphthaleneYield 76%

Reagents, catalysts & solvents 2

HCID 178418745HCID 178418745, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Cyclopropylmagnesium bromide (150 mL, 0.5M in tetrahydrofuran) was slowly added to a solution of 1-bromonaphthalene (10 g, 50 mmol) and [1,3-bis(diphenylphosphino)propane]dichloro nickel (II) in tetrahydrofuran (10 mL) stirred at 0° C., and the reaction mixture stirred at room temperature for 16 hours. The solvent was removed under reduced pressure and ethyl acetate and aqueous ammonium chloride were added. After extraction, the organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography to yield 1-cyclopropylnaphthalene (6.4 g, 76%).

Workup

  1. stirringthe reaction mixture stirred at room temperature for 16 hours
  2. customThe solvent was removed under reduced pressure and ethyl acetate and aqueous ammonium chloride
  3. additionwere added
  4. extractionAfter extraction
  5. dry with materialthe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f0b1ce71d8c44c1e81bc1b3bd2aae51c
Source dataset
uspto-grants-2012_08
Patent number
US08242154B2

Reaction notes

Loading…