Hydrogen Bromide → HCID 18976936, compound

HRID 2393689Notes

Reaction equation

HRID 2393689 reaction equation
COCCOCCO[CH2:9][CH2:10][CH:11]1[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2.[CH2:24]=[O:25].[C:26]([OH:29])(=O)C.[BrH:30].[BrH:31].[CH2:32]([O:34][C:35](=O)[CH3:36])[CH3:33].[CH3:38]CCCCC>O>[Br:30][CH2:9][C:10]1[CH:15]=[CH:16][C:17]2[C:18]3[C:19](=[CH:20][C:21]([CH2:38][Br:31])=[CH:22][CH:23]=3)[CH:13]([CH2:14][CH2:24][O:25][CH2:33][CH2:32][O:34][CH2:35][CH2:36][O:29][CH3:26])[C:12]=2[CH:11]=1

Participants

7

Reactant 5

HCID 260Hydrogen BromideHCID 712FormaldehydeHCID 21226206Ethyl acetate hexaneHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 53865880HCID 53865880, compound

Product 1

HCID 18976936HCID 18976936, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 1 L three-hole flask equipped with a stirrer, a thermometer and a reflux condenser, 31.2 g (0.1 mol) of 9-methoxyethoxyethoxyethylfluorene, 30 g (1.0 mol) of paraformaldehyde, 300 g of 30% HBr acetic acid solution, and 120 g of 48% HBr aqueous solution, were introduced and reacted for 24 hours at a temperature of 60° C. After reaction, the temperature was decreased to room temperature, and the reactant was diluted with 500 ml of cold water, and then extracted three times with 200 ml of dichloromethane. The extracted organic solutions were combined and washed consecutively with water, saturated NaHCO3 aqueous solution, and salt water. The resultant organic solution was dried with magnesium sulfate anhydride, and after filtering and evaporating the solvent, a light yellow viscous liquid was obtained. After refining the liquid using silica gel column (ethylacetate/hexan=1/4 mixed solvent), and evaporating the solvent, 39.8 g (yield: 80%) of a colorless transparent viscous liquid was obtained. [1H-NMR (CDCl3), δ 2.28(m, 3H, OCH3), 3.41-3.71(m, 12H, OCH2CH2), 4.09(t, 1H, CH), 4.60(s, 4H, CH2Br), 7.25-7.71(m, 6H, aromatic)].

Workup

  1. customreacted for 24 hours at a temperature of 60° C
  2. customAfter reaction
  3. customwas decreased to room temperature
  4. extractionextracted three times with 200 ml of dichloromethane
  5. washwashed consecutively with water, saturated NaHCO3 aqueous solution, and salt water
  6. dry with materialThe resultant organic solution was dried with magnesium sulfate anhydride
  7. filtrationafter filtering
  8. customevaporating the solvent
  9. customa light yellow viscous liquid was obtained
  10. customevaporating the solvent

Sources & evidence

ORD record
ord-ead3400845d8469bb40513206603936c
Source dataset
uspto-grants-1998_09
Patent number
US05807974

Reaction notes

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