1-Bromonaphthalene → 1-Cyclopropylnaphthalene

HRID 929606Notes

Reaction equation

HRID 929606 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-Cyclopropylnaphthalene

Reagents, catalysts & solvents 2

HCID 178418745HCID 178418745, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Cyclopropylmagnesium bromide was added to a solution of bromonaphthalene in tetrahydrofuran stirred at 0-5° C. in the presence of catalytic amount of [1,3-bis(diphenylphosphino)propane]dichloronickel(II) to form cyclopropylnaphthalene, which was diluted with ethyl acetate and washed.

Sources & evidence

ORD record
ord-fc672e6eabcd45a38a3e24052019a989
Source dataset
uspto-grants-2016_03
Patent number
US09296709B2

Reaction notes

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