Butyl Acrylate → HCID 58473636, compound

HRID 1845980Notes

Reaction equation

HRID 1845980 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[OH-:16].[Na+].CCCC[O:22][C:23]([CH:25]=[CH2:26])=[O:24]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1C=CC=CC=1.C(OCC)(=O)C>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([CH2:26][CH2:25][C:23]([OH:22])=[O:24])([CH2:26][CH2:25][C:23]([OH:22])=[O:16])[C:4]=2[CH:3]=1

Participants

7

Reactant 3

HCID 8846Butyl AcrylateHCID 14798Sodium HydroxideHCID 1400732,7-Dibromofluorene

Product 1

HCID 58473636HCID 58473636, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

After 2,7-dibromofluorene (8.02 g) and benzyltriethylammonium chloride (0.56 g) were dissolved in 30 mL of benzene, 8 mL of an aqueous 50% sodium hydroxide solution was added dropwise under a nitrogen atmosphere, followed by stirring for 15 minutes. N-butyl acrylate (12.65 g) was added dropwise and the mixture was reacted at room temperature for 5 hours. The reaction solution was diluted with 200 mL of ethyl acetate, washed three times with water, washed once with brine, and then the organic layer was dried over magnesium sulfate. The solution was filtered and the solvent was distilled off. The solution was purified by silica gel column chromatography using dichloromethane as an eluent and then recrystallized from hexane to obtain (2,7-dibromo)-9H-fluorene-9,9-dipropionic acid (F2COOBuBr2) (7.87 g, 55%).

Workup

  1. customthe mixture was reacted at room temperature for 5 hours
  2. washwashed three times with water
  3. washwashed once with brine
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. filtrationThe solution was filtered
  6. distillationthe solvent was distilled off
  7. customThe solution was purified by silica gel column chromatography
  8. customrecrystallized from hexane

Sources & evidence

ORD record
ord-4dac6ab8a9164b7fa8cda68b231f7ed1
Source dataset
uspto-grants-2015_02
Patent number
US08951646B2

Reaction notes

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