Ethyl Acetate → HCID 68226825, compound

HRID 1952637Notes

Reaction equation

HRID 1952637 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:11]Br)=[CH:8][C:9]=1[Br:10])=[O:4].C([O-])(O)=[O:14].[Na+].CCOC(C)=O>CS(C)=O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:11][OH:14])=[CH:8][C:9]=1[Br:10])=[O:4]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 68226878HCID 68226878, compound

Product 1

HCID 68226825HCID 68226825, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 3-Bromo-5-bromomethyl-thiophene-2-carboxylic acid methyl ester (0.99 g, 3.15 mmol) and NaHCO3 (4.5 g, 53.6 mmol) in DMSO (25 ml) was heated at 115° C. for 3 h. The reaction mixture was cooled. The reaction mixture was EtOAc (250 ml), washed with brine, dried over sodium sulfate, filtered and evaporated. The residue was purified by column (0-30% EtOAc in hexane) to give 0.19 g (24%) yellow solid product.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column (0-30% EtOAc in hexane)

Sources & evidence

ORD record
ord-a42f51893f9644af997ff695ee2fd510
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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