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

HRID 29393Notes

Reaction equation

[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([Br:19])=[C:14]([OH:18])[C:11]=2[C:12]=1[CH3:13])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To 200 mg (0.81 mmol) of 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester was added 2 mL of carbon tetrachloride. The mixture was cooled with water/ice bath while 1 equivalent of N-bromosuccinimide was added in small portions. After stirring at 0° C. for 6 h, the reaction mixture was filtered and the filtrate was loaded onto a column and purified by column chromatography to give 225 mg (85% yield) of 5-bromo-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid tert-butyl ester as a white solid.

Workup

additionwas added in small portions
filtrationthe reaction mixture was filtered
custompurified by column chromatography

Sources & evidence

ORD record: ord-92910cad295f41189c90bd36fc0e5e9e
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07420001B2

Reaction notes

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