Sodium Hydroxide → 2-(4-Bromothiophen-2-yl)acetic acid

Reaction equation

[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH2:9][C:10]([O:12]CC)=[O:11])[S:7][CH:8]=1>>[Br:3][C:4]1[CH:5]=[C:6]([CH2:9][C:10]([OH:12])=[O:11])[S:7][CH:8]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 21260738Ethyl 4-bromo-2-thiopheneacetate

Product 1

HCID 212607302-(4-Bromothiophen-2-yl)acetic acidYield 96.5%

Procedure

12 ml of 10% aqueous sodium hydroxide solution was added to the 4.94 g (19.8 mmol) of ethyl 4-bromo-2-thiopheneacetate and stirring carried out for 5 hours at 90° C. The reaction liquid was then cooled and extracted with ether. The aqueous layer was neutralized with hydrochloric acid, extracted with ether, then dried and concentrated. 4.24 g (19.1 mmol, 96%) of 4-bromo-2-thiopheneacetic acid was obtained.

Workup

customThe reaction liquid
temperaturewas then cooled
extractionextracted with ether
extractionextracted with ether
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-e9db741ce31f49bcaddc0e681c0b7856
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184245B2

Reaction notes

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