N-bromobutanimide → 5-Bromo-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 29398Notes

Reaction equation

HRID 29398 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([Br:17])=[C:12]([OH:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 748649Ethyl 4-hydroxy-3-methyl-1-benzofuran-2-carboxylate

Product 1

HCID 125429705-Bromo-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl esterYield 59%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

To 2 g (0.81 mmol) of 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester was added 20 mL of carbon tetrachloride, and the mixture was cooled with a water/ice bath while 1 equivalent of N-bromosuccinimide was added in small portions. After stirring at 0° C. for 3 h, the reaction mixture was filtered and the filtrate was loaded onto a column and purified by column chromatography to give 1.6 mg (59% yield) of 5-bromo-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester as a white solid.

Workup

  1. additionwas added in small portions
  2. filtrationthe reaction mixture was filtered
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-4f269259c42b4782b33880fbbe459e37
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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