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Water → 5-Fluorothiophene-2-carboxylic acid

HRID 1870498
Notes
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Reaction equation

HRID 1870498 reaction equation
[F:1][C:2]1[S:6][C:5]([C:7]#N)=[CH:4][CH:3]=1.[OH-:9].[Na+].[OH2:11]>>[F:1][C:2]1[S:6][C:5]([C:7]([OH:11])=[O:9])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 108987265-fluorothiophene-2-carbonitrile

Product 1

HCID 118049015-Fluorothiophene-2-carboxylic acidYield 82%

Procedure

A mixture of the title product of Example 1 (1.5 g, 11.8 mmol) and 1.0 N NaOH (25 mL, 25 mmol) was refluxed for 3 hours. The mixture was poured into water (200 mL) and washed two times with 200 mL diethyl ether. The aqueous extract was acidified with 1N hydrochloric acid to pH 1, then extracted two times with 200 mL methylene chloride. The organic extracts were combined, washed with water (80 mL), dried (MgSO4) and concentrated in vacuo to give a solid. Trituration with hexanes afforded 1.2 g (82%) of the title product as a white solid, mp 140-2° C. 1H-NMR (d6 -DMSO): δ7.47 (m, 1H), 6.84 (m, 1H). Anal. Calcd. for C5H3O2SF: C, 41.10; H, 2.07. Found: C, 41.16; H, 1.98.

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes

Workup

  1. temperaturewas refluxed for 3 hours
  2. washwashed two times with 200 mL diethyl ether
  3. extractionThe aqueous extract
  4. extractionextracted two times with 200 mL methylene chloride
  5. washwashed with water (80 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give a solid

Sources & evidence

ORD record
ord-90a9c5d37fba4e8b890e4c980fd13889
Source dataset
uspto-grants-2000_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06096901

Reaction notes

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