Hydrochloric Acid → 3-Bromofuran-2-carboxylic acid

HRID 1747754

Reaction equation

HRID 1747754 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[CH:7]=[O:8].CC(=CC)C.Cl([O-])=[O:15].[Na+].P([O-])(O)(O)=O.[Na+].Cl>C(O)(C)(C)C.O>[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([OH:15])=[O:8]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 105532-Methyl-2-buteneHCID 33672713-Bromo-2-furaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 6054793-Bromofuran-2-carboxylic acidYield 74.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of 3-bromofuran-2-carbaldehyde (25.0 g) and 2-methyl-2-butene (45.4 mL) in tert-butanol (250 mL) was added dropwise a solution of 80% sodium chlorite (40.5 g) and sodium dihydrogen phosphate (51.5 g) in water (350 mL) at room temperature, and the mixture was stirred overnight. To the reaction mixture was added 1M hydrochloric acid (300 ml), and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was washed with hexane/ethyl acetate (5/1) and recrystallized from hexane/ethyl acetate to give the title compound (20.3 g). 1H NMR (300 MHz, CDCl3) δ 6.66 (1H, d, J=1.9 Hz), 7.58 (1H, d, J=1.9 Hz).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe residue was washed with hexane/ethyl acetate (5/1)
  6. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-bfca6aa4fa6b4082b649bed729f7b7c1
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Linked notes

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