Ethyl bromoacetate → HCID 22228630, compound

HRID 1744285Notes

Reaction equation

HRID 1744285 reaction equation
[Br:1][C:2]1[C:3]([OH:13])=[C:4]([CH:7]=[C:8]([Br:12])[C:9]=1[O:10][CH3:11])[CH:5]=O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CN(C=O)C>[Br:12][C:8]1[C:9]([O:10][CH3:11])=[C:2]([Br:1])[C:3]2[O:13][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5][C:4]=2[CH:7]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 35066233,5-Dibromo-2-hydroxy-4-methoxybenzaldehyde

Product 1

HCID 22228630HCID 22228630, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

16 g (51,6 mmol) of 3,5-dibromo-2-hydroxy-4-methoxybenzaldehyde (Biorg. Med. Chem. 1998, 6, 1153–1162) and 17.84 g (129 mmol) of potassium carbonate are initially introduced in DMF and 8.62 g (51.6 mmol) of ethyl bromoacetate are then added dropwise to the mixture. The latter is stirred at 80° C. for 6 hours and then poured onto ice water after having been cooled; the precipitate is filtered off with suction. The precipitate is washed with water and dried. 15.47 g (79%) of ethyl 5,7-dibromo-6-methoxy-1-benzofuran-2-carboxylate are obtained.

Workup

  1. additionpoured onto ice water
  2. temperatureafter having been cooled
  3. filtrationthe precipitate is filtered off with suction
  4. washThe precipitate is washed with water
  5. customdried

Sources & evidence

ORD record
ord-d774256c4f2240b08d1586f3e422d379
Source dataset
uspto-grants-2006_03
Patent number
US07015246B2

Reaction notes

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