Iodine → 2-Iodofuran-3-carboxylic acid

HRID 1750322

Reaction equation

HRID 1750322 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=[O:7])=[CH:2]1.[Li]CCCC.[I:14]I.O>O1CCCC1>[I:14][C:2]1[O:1][CH:5]=[CH:4][C:3]=1[C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 102683-Furoic acidHCID 178418339Butyllithium

Product 1

HCID 685630822-Iodofuran-3-carboxylic acidYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirring solution of furan-3-carboxylic acid (5 g, 44.6 mmol) in anhydrous tetrahydrofuran (200 ml) under a nitrogen atmosphere at −78° C. was added BuLi (44.6 ml, 112 mmol) dropwise. After stirring for 0.5 h, cooling was switched off and the mixture allowed to warm to room temperature. During warming, iodine (12.5 g, 49.1 mmol) as a solution in anhydrous tetrahydrofuran (30 ml) and added dropwise to the stirring mixture. Water was added (100 ml) and the organic solvents were removed in vacuo. The aqueous solution was acidified to ca pH 1 using 2M hydrochloric acid (aq) solution (ca 10-20 ml). The precipitated solid was collected by filtration and dried under vacuum and flowing nitrogen for 16 h to afford the title compound (6.21 g, 59%) that was used in the next step without further purification. LCMS RT=0.78 min, M−H−=236.8.

Workup

  1. temperaturecooling
  2. temperatureDuring warming
  3. customthe organic solvents were removed in vacuo
  4. filtrationThe precipitated solid was collected by filtration
  5. customdried under vacuum
  6. customfor 16 h

Sources & evidence

ORD record
ord-0228e03bae034da181e4bed1a9295070
Source dataset
uspto-grants-2015_10
Patent number
US09156853B2

Linked notes

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