1-Bromooctane → HCID 71148905, compound

HRID 1504302Notes

Reaction equation

HRID 1504302 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:17][CH2:16][C:7]3=[CH:8][C:9]([Br:15])=[CH:10][C:11]4[NH:12][C:13]([CH:14]=1)=[C:5]2[C:6]=43.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[CH2:19]([N:12]1[C:13]2[CH:14]=[C:2]([Br:1])[CH:3]=[C:4]3[CH2:17][CH2:16][C:7]4[C:6]([C:5]=23)=[C:11]1[CH:10]=[C:9]([Br:15])[CH:8]=4)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 81401-BromooctaneHCID 14798Sodium HydroxideHCID 67384983HCID 67384983, compound

Product 1

HCID 71148905HCID 71148905, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Procedure

A dried flask fitted with a condenser was charged with 2,6-dibromo-8,9-dihydro-4H-benzo[def]carbazole (1.2) (3.50 g, 9.97 mmol), bromooctane (1.9 cm3, 11.0 mmol), tetrabutylammonium bromide (0.161 g, 0.500 mmol), freshly powdered sodium hydroxide (0.798 g, 19.9 mmol) and acetone (100 cm3). The resulting solution was reflux for 4 hours and then poured into distilled water (100 cm3). The resulting solution was extracted with dichloromethane (3×200 cm3). The combined organic fractions were dried over magnesium sulfate and the solvent was removed under reduced pressure. The crude product was dissolved in dichloromethane, pre-adsorbed on silica gel, and purified by column chromatography (90:10 petroleum ether:ethyl acetate as eluent) resulting in a off-white solid. (3.29 g, yield 71.2%): NMR (1H, 300 MHz, CDCl3): δ 7.26 (s, 2H); 7.08 (s, 2H); 4.06(t, J=7.1 Hz, 2H); 3.22 (s, 4H); 1.81 (m, 4H); 1.28 (m, 10H); 0.86 (t, J=6.8 Hz, 3H).

Workup

  1. customA dried flask fitted with a condenser
  2. temperatureThe resulting solution was reflux for 4 hours
  3. additionpoured
  4. distillationinto distilled water (100 cm3)
  5. extractionThe resulting solution was extracted with dichloromethane (3×200 cm3)
  6. dry with materialThe combined organic fractions were dried over magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. dissolutionThe crude product was dissolved in dichloromethane, pre-adsorbed on silica gel
  9. custompurified by column chromatography (90:10 petroleum ether:ethyl acetate as eluent)
  10. customresulting in a off-white solid

Sources & evidence

ORD record
ord-fd1729e5aeed48019b30b89bee50b660
Source dataset
uspto-grants-2015_12
Patent number
US09212260B2

Reaction notes

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