ChemicalBook CAS DataBase List 3-Bromofuran-2-carboxylic acid

3-Bromofuran-2-carboxylic acid synthesis

4synthesis methods

Product Name:3-Bromofuran-2-carboxylic acid
CAS Number:14903-90-3
Molecular formula:C5H3BrO3
Molecular Weight:190.98

14757-78-9 Synthesis

14757-78-9
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$21.00/250mg

14903-90-3
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$33.00/100mg

Yield: 20.3 g

Reaction Conditions:

with sodium chlorite;sodium dihydrogenphosphate in water;tert-butyl alcohol at 20;

Steps:

1.A A) 3-bromofuran-2-carboxylic acid
A)
3-bromofuran-2-carboxylic acid
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).

References:

Taniguchi, Takahiko;Suzuki, Shinkichi;Yoshikawa, Masato;Hasui, Tomoaki;Fushimi, Makoto;Kunitomo, Jun US2013/137675, 2013, A1 Location in patent:Paragraph 0598