Carbon Tetrachloride → 5,7-Dichloro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 29388Notes

Reaction equation

HRID 29388 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14]C=[C:12]([OH:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[Cl:17]N1C(=O)CCC1=O.[C:25]([Cl:29])(Cl)(Cl)Cl>>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[C:15]([Cl:17])=[CH:14][C:25]([Cl:29])=[C:12]([OH:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 5943Carbon Tetrachloride2×HCID 31398ChlorosuccinimideHCID 748649Ethyl 4-hydroxy-3-methyl-1-benzofuran-2-carboxylate

Product 1

HCID 687122235,7-Dichloro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl esterYield 30%

Conditions

Temperature
-10 °C

Procedure

To 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester (0.5 g, 2.27 mmol) was added 5 mL of carbon tetrachloride, carbon tetrachloride, and the mixture was cooled with an ethanol/ice bath while 1 equivalent of N-chlorosuccinimide was added in small portions. After stirring at −10° C. for 3 h, the reaction mixture was filtered and the filtrate was loaded onto a silica gel column. Chromatography gave 190 mg (30% yield) of 5,7-dichloro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester as an off-white solid.

Workup

  1. additionwas added in small portions
  2. filtrationthe reaction mixture was filtered

Sources & evidence

ORD record
ord-ec0aff54a8214c74a476d7e086f834fd
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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