Hydrochloric Acid → HCID 22630272, compound

HRID 2416354Notes

Reaction equation

HRID 2416354 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([OH:15])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[CH2:16](Br)[CH2:17][CH2:18][CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 80571-BromopentaneHCID 11430Potassium CarbonateHCID 2635827-bromo-9h-fluoren-2-ol

Product 1

HCID 22630272HCID 22630272, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-bromo-7-hydroxyfluorene (18 g), pentyl bromide (15.1 g), potassium carbonate (26.6 g) and dimethylformamide (200 mL) was heated for 3 hours while refluxing. 6M-hydrochloric acid (100 mL) was added to the reaction solution, and the solution was extracted with toluene. The toluene layer was washed with water and then dried on anhydrous magnesium sulfate, and it was concentrated under reduced pressure. This concentrate was recrystallized from acetone to obtain 2-bromo-7-pentyloxyfluorene (20 g) of colorless needle crystal.

Workup

  1. temperaturewas heated for 3 hours
  2. temperaturewhile refluxing
  3. extractionthe solution was extracted with toluene
  4. washThe toluene layer was washed with water
  5. dry with materialdried on anhydrous magnesium sulfate, and it
  6. concentrationwas concentrated under reduced pressure
  7. customThis concentrate was recrystallized from acetone

Sources & evidence

ORD record
ord-dc2c21851cfa4c6dafb79ba8bdc9686d
Source dataset
uspto-grants-2004_11
Patent number
US06824709B2

Reaction notes

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