Chlorosuccinimide → 5-Chloro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 29383Notes

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].[Cl: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]([Cl:17])=[C:12]([OH:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

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, 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 259 mg (48% yield) of 5-chloro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester as an off-white solid.

Workup

additionwas added in small portions
filtrationthe reaction mixture was filtered

Sources & evidence

ORD record: ord-2aa65abbca3b4cd083394450999cb7f1
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420001B2

Reaction notes

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