Methyl Acrylate → HCID 22475898, compound

HRID 2282348Notes

Reaction equation

HRID 2282348 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.[C:16]([O:20][CH3:21])(=[O:19])[CH:17]=[CH2:18].[OH-:22].[Na+]>C1(C)C=CC=CC=1>[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]([CH2:18][CH2:17][C:16]([O:20][CH3:21])=[O:22])([CH2:18][CH2:17][C:16]([O:20][CH3:21])=[O:19])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 14798Sodium HydroxideHCID 1400732,7-Dibromofluorene

Product 1

HCID 22475898HCID 22475898, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

2,7-Dibromofluorene (1 g, 3.1 mmol), methyl acrylate (861 mg, 10 mmol) tetrabutylammonium bromide (100 mg, 0.3 mmol) and toluene (5 mL) were added to a small round bottom flask with a Teflon-coated stirbar. Next 2 mL of 50% NaOH (aq) is added while stirring. The reaction is allowed to proceed overnight. The next day the toluene layer is transferred to a flask and the aqueous layer extracted with two portions of toluene. The organic layers are combined, dried with Mg2SO4, and filtered. Silica (2 g) is added to the filtrate and the solution is evaporated. The product is obtained as a white solid (1.23 g, 80% yield) after purification by column chromatography.

Workup

  1. extractionthe aqueous layer extracted with two portions of toluene
  2. dry with materialdried with Mg2SO4
  3. filtrationfiltered
  4. additionSilica (2 g) is added to the filtrate
  5. customthe solution is evaporated

Sources & evidence

ORD record
ord-7c38cec097454ed29e9db85d5e1ef3f3
Source dataset
uspto-grants-2015_09
Patent number
US09139869B2

Reaction notes

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