1-(3-Bromophenyl)-2,5-dihydro-1H-pyrrole → 2,5-Dihydro-1-[3-(phenylmethyl)phenyl]-1H-pyrrole

HRID 2216355Notes

Reaction equation

HRID 2216355 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][CH:11]=[CH:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[CH2:13]([Mg]Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CC(P(C1C=CC=CC=1)C1C=CC=CC=1)C.C1C=CC(PC2C=CC=CC=2)=CC=1.[Cl-].[Ni].O1CCCC1>[CH2:13]([C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][CH:11]=[CH:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 177499441-(3-Bromophenyl)-2,5-dihydro-1H-pyrroleHCID 178418336HCID 178418336, compound

Product 1

HCID 219423032,5-Dihydro-1-[3-(phenylmethyl)phenyl]-1H-pyrrole

Reagents, catalysts & solvents 2

HCID 21654969Diphenylphosphane;diphenyl(propan-2-yl)phosphane;nickel;chlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 6.6 g of 1-(3-bromophenyl)-2,5-dihydropyrrole, 800 mg of 1,3-bis(diphenylphosphino)propanenickel (II) chloride and 40 ml of tetrahydrofuran was added dropwise 22 ml of a 2.0 M tetrahydrofuran solution of benzyl magnesium chloride, followed by stirring overnight as it was. The reaction mixture was separated with a saturated aqueous ammonium chloride solution-ethyl acetate, and the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and then evaporated. The residue was purified by silica gel column chromatography with 1% ethyl acetate/hexane, to give 2.1 g of the title compound.

Workup

  1. customThe reaction mixture was separated with a saturated aqueous ammonium chloride solution-ethyl acetate
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography with 1% ethyl acetate/hexane

Sources & evidence

ORD record
ord-71eb1f86b9654b1191daaf81f337db63
Source dataset
uspto-grants-2006_09
Patent number
US07112593B2

Reaction notes

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