Water → HCID 22066277, compound

HRID 1760503Notes

Reaction equation

HRID 1760503 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5](OCCCCCCCC)=[CH:4][C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:18]=1.[C:32]([Li])([CH3:35])([CH3:34])C.[Br:37][C:38]1[CH:50]=[CH:49][C:48]2[C:47]3[C:42](=[CH:43][C:44]([Br:51])=[CH:45][CH:46]=3)[C:41](=[O:52])[C:40]=2[CH:39]=1.[OH2:53]>C1COCC1.[Cl-].[Na+].O>[CH2:24]([O:23][C:19]1[CH:20]=[CH:21][C:22]([C:41]2([OH:52])[C:40]3[CH:39]=[C:38]([Br:37])[CH:50]=[CH:49][C:48]=3[C:47]3[C:42]2=[CH:43][C:44]([Br:51])=[CH:45][CH:46]=3)=[C:17]([C:3]2[CH:4]=[CH:5][C:6]([O:53][CH2:4][CH2:3][CH2:2][CH2:7][CH2:6][CH2:34][CH2:32][CH3:35])=[CH:7][CH:2]=2)[CH:18]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

7

Reactant 4

HCID 962WaterHCID 2599222,7-Dibromo-9-fluorenoneHCID 22066270HCID 22066270, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 22066277HCID 22066277, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-78 °C

Procedure

2-bromo-5,3′-bis-octyloxy-biphenyl (0.598 g, 1.225 mmol) prepared in Example 3 was dissolved in dried THF (30 ml) and cooled to −78° C. Then, t-butyllithium (t-BuLi) (1.7M, 1.44 ml, 2.45 mmol) was added slowly. The obtained resultant was stirred for about 1 hour at −78° C. After 1 hour, 2,7-dibromofluorene-9-one (0.497 g, 1.47 mmol) dissolved in dried THF (20 ml) was added slowly, stirred for about 1 hour, allowed to warm to room temperature and further stirred at room temperature for about 30 minutes. A small amount of distilled water was added to complete the reaction and saturated brine was added to the resultant. The organic layer was filtered twice with ether and dried over sulfate, and the ether was concentrated under reduced pressure. Purification by silica gel chromatography using 30 to 40% dichloromethane in hexane gave 9-(5,4′-bis-octyloxy-biphenyl-2-yl)-2,7-dibromo-9H-fluorene-9-ol corresponding to the compound IV of the reaction scheme 2 (Yield: 0.62 g, 68%), R1 and R2 in the formula of the compound IV being each independently octyl and Y1 and Y2 being bromine. The product was identified through the NMR spectrum and element analysis that it had the identical structure with the compound IV.

Workup

  1. customThe obtained resultant
  2. waitAfter 1 hour
  3. additionwas added slowly
  4. stirringstirred for about 1 hour
  5. temperatureto warm to room temperature
  6. stirringfurther stirred at room temperature for about 30 minutes
  7. additionwas added to the resultant
  8. filtrationThe organic layer was filtered twice with ether
  9. dry with materialdried over sulfate
  10. concentrationthe ether was concentrated under reduced pressure
  11. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-c313aec9dbaf459eb50a1ca01f8348f3
Source dataset
uspto-grants-2005_01
Patent number
US06844088B2

Reaction notes

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