Sodium Carbonate → HCID 68599131, compound

HRID 1895846Notes

Reaction equation

HRID 1895846 reaction equation
[Br:1][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]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)#[N:29].C([O-])([O-])=O.[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([C:33]4[CH:34]=[CH:35][C:30]([C:28]#[N:29])=[CH:31][CH:32]=4)=[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

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 35396479,9-Dihexyl-2,7-dibromofluorene

Product 1

HCID 68599131HCID 68599131, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

4-(2-bromo-9,9-dihexyl-9H-fluoren-7-yl)benzonitrile was prepared through the following procedure. A mixture of 2,7-dibromo-9,9-dihexyl-9H-fluorene (0.985 g, 2 mmol), 4-cyanophenylboronic acid (0.146 g, 1 mmol), and tetrakis(triphenylphosphine) palladium (11.6 mg, 0.01 mmol) were added to an air-free two-phase mixture of toluene (25 mL) and aqueous 2M Na2CO3 solution (15 mL). The resulting mixture was vigourously stirred under argon atmosphere at 110° C. for 24 hours. The organic layer was separated and the aqueous phase was extracted with ether. The organic layers were washed with brine (2×50 mL), and dried with anhydrous MgSO4. The solvent was evaporated and the residue passed through a silica-gel column. 0.27 g of pure product were obtained by recrystallization in heptane with a yield of 51%. 1H NMR (400 MHz, CDCl3): δ(ppm) 7.766-7.751 (m, 5H), 7.605-7.583 (d, J=8.8 Hz, 1H), 7.583-7.564 (d, J=7.6 Hz, 1H), 7.524 (s, 1H), 7.495-7.476 (m, 2H), 2.013-1.964 (m, 4H), 1.140-1.053 (m, 12H), 0.781-0.746 (t, J=7.0 Hz, 6H), 0.658-0.624 (m, 4H).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous phase was extracted with ether
  3. washThe organic layers were washed with brine (2×50 mL)
  4. dry with materialdried with anhydrous MgSO4
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a61191a88c3c43d8800a0895765f796f
Source dataset
uspto-grants-2013_08
Patent number
US08518559B2

Reaction notes

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