N-methyl-2-pyrrolidone → HCID 68549539, compound

HRID 2244961Notes

Reaction equation

HRID 2244961 reaction equation
Br[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=3)[C:5]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:4]=2[CH:3]=1.[C:28]([Cu])#[N:29].[CH3:31][N:32]1C(=O)CCC1>>[C:31]([C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([C:28]#[N:29])=[CH:9][CH:10]=3)[C:5]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:4]=2[CH:3]=1)#[N:32]

Participants

4

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 35396479,9-Dihexyl-2,7-dibromofluoreneHCID 178418546HCID 178418546, compound

Product 1

HCID 68549539HCID 68549539, compound

Conditions

Temperature
90 °C

Procedure

A mixture of 2,7-dibromo-9,9-dihexylfluorene (10 mmol) and CuCN (35 mmol) in NMP (30 mL) was purged with argon and refluxed for 4 h. The hot reaction mixture (˜120° C.) was then slowly poured into a stirred acidified aqueous FeCl3 solution. The mixture was stirred for additional 20 min at 90° C. and then extracted with toluene. The combined organic layer was washed with HCl until the dark heavy organic layer disappeared, and then with water, 10% NaOH solution, and water again until pH reaches about 7. It was dried over anhydrous MgSO4. After removal of the solvent, the residue was purified by column chromatography on silica gel using AcOEtand hexane (20/80) as the eluent, followed by recrystallization from hexane to afford colourless crystals in yield of 3.21 g (83.35%). M.P.=116-118° C.

Workup

  1. customwas purged with argon
  2. temperaturerefluxed for 4 h
  3. additionThe hot reaction mixture (˜120° C.) was then slowly poured into a stirred
  4. extractionextracted with toluene
  5. washThe combined organic layer was washed with HCl until the dark heavy organic layer
  6. dry with materialIt was dried over anhydrous MgSO4
  7. customAfter removal of the solvent
  8. customthe residue was purified by column chromatography on silica gel using AcOEtand hexane (20/80) as the eluent
  9. customfollowed by recrystallization from hexane
  10. customto afford colourless crystals in yield of 3.21 g (83.35%)

Sources & evidence

ORD record
ord-e84bebf0c95449c3bf7fe716c3d0bc03
Source dataset
uspto-grants-2010_03
Patent number
US07679082B2

Reaction notes

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