Water → 2-Bromo-4-thienyl-methoxyethyl methacrylate

HRID 5050

Reaction equation

HRID 5050 reaction equation
[Br:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][O:8][CH2:9]CO)[CH:6]=1.N1C=CC=C[CH:13]=1.C(#N)C.[C:21](Cl)(=[O:25])[C:22]([CH3:24])=[CH2:23].[OH2:27]>C(OCC)(=O)C>[C:21]([O:25][CH2:13][CH:7]([C:5]1[CH:6]=[C:2]([Br:1])[S:3][CH:4]=1)[O:8][CH3:9])(=[O:27])[C:22]([CH3:24])=[CH2:23]

Participants

7

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 6342AcetonitrileHCID 13528Methacryloyl chlorideHCID 197977502-Bromo-4-2-hydroxyethoxymethylthiophene

Product 1

HCID 570171242-Bromo-4-thienyl-methoxyethyl methacrylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

While stirring a mixture of 0.1 mol of 2-bromo-4-2-hydroxyethoxymethylthiophene, 0.1 mol of pyridine, and 100 ml of acetonitrile at a temperature of lower than 10° C., 0.1 mol of methacryloyl chloride was added dropwise to the mixture over a period of 30 minutes. After stirring the mixture for one hour, 200 ml of ethyl acetate and 200 ml of water were added to the mixture. The ethyl acetate layer was extracted, concentrated, and purified by column chromatography to provide 22.1 g of 2-bromo-4-thienyl-methoxyethyl methacrylate (5-A).

Workup

  1. stirringAfter stirring the mixture for one hour
  2. extractionThe ethyl acetate layer was extracted
  3. concentrationconcentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-65ea4057d75b4366aba54ef2265871f0
Source dataset
uspto-grants-1993_09
Patent number
US05243004

Linked notes

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