Ethyl Bromide → 6-Ethoxy-benzofuran-3-carboxylic acid ethyl ester

HRID 1804789Notes

Reaction equation

HRID 1804789 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[O:8][CH:7]=1)=[O:5])[CH3:2].Br[CH2:17][CH3:18].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15][CH2:17][CH3:18])=[CH:14][C:9]=2[O:8][CH:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 10796Cesium carbonateHCID 59152646HCID 59152646, compound

Product 1

HCID 673618076-Ethoxy-benzofuran-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

6-Hydroxy-benzofuran-3-carboxylic acid ethyl ester (26) (8 g, 39 mmol) is dissolved in 80 ml of DMF and after addition of bromoethane (5.8 ml, 78 mmol) and Cs2CO3 (15.2 g, 46.6 mmol) the mixture is stirred for 2 h at 100° C. After evaporation of the mixture at high vacuum, the residue is dissolved in ethyl acetate, washed with water and with brine, dried over sodium sulfate and evaporated under reduced pressure. The yellow solid is used in the next step without further purification.

Workup

  1. customAfter evaporation of the mixture at high vacuum
  2. dissolutionthe residue is dissolved in ethyl acetate
  3. washwashed with water and with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure
  6. customThe yellow solid is used in the next step without further purification

Sources & evidence

ORD record
ord-57a15d263bef433da12b9270a65e82a7
Source dataset
uspto-grants-2013_01
Patent number
US08354431B2

Reaction notes

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