Dimethylformamide → 2-Phenyl-1H-indene

HRID 650313Notes

Reaction equation

HRID 650313 reaction equation
CN(C=O)C.[CH2:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7]1.I[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>CC([O-])=O.CC([O-])=O.[Pd+2].O.ClCCl>[C:16]1([C:7]2[CH2:8][C:9]3[C:14]([CH:6]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 7219IndeneHCID 8471TriethylamineHCID 11575Iodobenzene

Product 1

HCID 3534352-Phenyl-1H-indene

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

20 ml of DMF, 2.2 g (20 mmol) of indene, 2.2 ml (20 mmol) of iodo-benzene, 2 ml of triethylamine and 0,134 (0,6 mmol) of Pd(OAc)2 were stirred under reflux for 10 hours. The resulting mixture was poured into the mixture of 50 ml of dicloromethane and 50 ml of water. Organic layer was separated, washed twice with water, filtered and dried over Na2SO4. Dicloromethane was removed and the residue was recrystallized from 20 ml of EtOH. The yeld of product was 65 %.

Workup

  1. temperatureunder reflux for 10 hours
  2. customOrganic layer was separated
  3. washwashed twice with water
  4. filtrationfiltered
  5. dry with materialdried over Na2SO4
  6. customDicloromethane was removed
  7. customthe residue was recrystallized from 20 ml of EtOH

Sources & evidence

ORD record
ord-4b1b2c56ca564ff9a66078fbe31961df
Source dataset
uspto-grants-2001_08
Patent number
US06271411B1

Reaction notes

Loading…