Formaldehyde → Ethyl 2-(4-bromophenyl)acrylate

HRID 220190Notes

Reaction equation

HRID 220190 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)[CH3:2].C=O.[C:16]([O-])([O-])=O.[K+].[K+]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-].CN(C=O)C.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:13])[C:5]([C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][CH:7]=1)=[CH2:16])[CH3:2]

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 7020609Ethyl 2-(4-bromophenyl)acetate

Product 1

HCID 11470828Ethyl 2-(4-bromophenyl)acrylateYield 73%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (4-bromo-phenyl)-acetic acid ethyl ester (972.4 mg, 4 mmol), paraformaldehyde (240 mg, 8 mmol), and Bu4NCl (22 mg, 0.08 mmol) in DMF (10 mL) was added K2CO3 (1.32 g, 9.6 mmol). This mixture was heated at 60 degrees Celsius for 2 h. Then the mixture was cooled and diluted with EtOAc (30 mL) and washed with water (20 mL×3), brine, dried over Na2SO4, filtered and evaporated. The residue was purified by flash column chromatography on silica gel to give a white solid (0.74 g, 73%). MS: calc'd 255 (MH+), exp 255 (MH+).

Workup

  1. temperatureThis mixture was heated at 60 degrees Celsius for 2 h
  2. temperatureThen the mixture was cooled
  3. washwashed with water (20 mL×3), brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-2924d033d258401fa7149898a5d9ffb3
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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