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