1-Bromooctane → 6,6,12,12-Tetraoctyl-6,12-dihydroindeno[1,2-b]fluorene

HRID 1488319Notes

Reaction equation

HRID 1488319 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[CH:10]=[C:9]4[C:14]5[C:19]([CH2:20][C:8]4=[CH:7][C:6]=3[C:5]=2[CH:4]=[CH:3][CH:2]=1)=[CH:18][CH:17]=[CH:16][CH:15]=5.C[C:22]([CH3:25])([O-])[CH3:23].[Na+].[CH2:27](Br)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>CS(C)=O.CCCCCCC.CO>[CH2:27]([C:20]1([CH2:5][CH2:13][CH2:1][CH2:2][CH2:3][CH2:23][CH2:22][CH3:25])[C:8]2[C:9](=[CH:10][C:11]3[C:12]([CH2:15][CH2:14][CH2:9][CH2:10][CH2:11][CH2:6][CH2:7][CH3:8])([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[C:13]4[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=4[C:6]=3[CH:7]=2)[C:14]2[C:19]1=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

7

Reactant 3

HCID 81401-BromooctaneHCID 15559295Indeno[1,2-b]fluorene, 6,12-dihydro-HCID 23676156Sodium t-butoxide

Product 1

HCID 247643156,6,12,12-Tetraoctyl-6,12-dihydroindeno[1,2-b]fluorene

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 8900HeptaneSolvent

Conditions

Temperature
80 °C

Procedure

6,12-Dihydroindeno[1,2-b]fluorene (24.03 g) was dissolved in DMSO (372.4 mL, Sigma-Aldrich) and sodium tert-butoxide (56.18 g) was added before heating to 80° C. Octyl bromide (110.6 g, Fluorochem) was added dropwise keeping the temperature below 90° C. The reaction was cooled, dissolved in heptane (2400 mL), washed with water (3×746 mL), dried (Na2SO4) and concentrated to give a dark solid. The solid was refluxed in methanol (480 mL) for 10 minutes, cooled to room temperature and collected by vacuum filtration. The solids were washed with methanol (2×480 mL) and dried to give the product as a dark solid. Yield; 82.56 g. 1H NMR (400 MHz, CDCl3); 7.74 (2H, m), 7.60 (2H, m), 7.32 (6H, m), 2.00 (8H, m), 1.05 (40H, m), 0.80 (12H, m), 0.60 (8H, m).

Workup

  1. customthe temperature below 90° C
  2. temperatureThe reaction was cooled
  3. washwashed with water (3×746 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a dark solid
  7. temperaturecooled to room temperature
  8. filtrationcollected by vacuum filtration
  9. washThe solids were washed with methanol (2×480 mL)
  10. customdried

Sources & evidence

ORD record
ord-221cdf6fe5d44092afebb3c096560749
Source dataset
uspto-grants-2016_08
Patent number
US09431145B2

Reaction notes

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