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ChemicalBook CAS DataBase List 3-bromo-2-hydroxycyclopent-2-en-1-one

3-bromo-2-hydroxycyclopent-2-en-1-one synthesis

5synthesis methods
-

Yield:3019-83-8 89%

Reaction Conditions:

with N-Bromosuccinimide in water;acetone at 20; for 16 h;

Steps:

4.2. 3-Bromo-2-hydroxy-cyclopent-2-enone (1)

To a solution of 1,2-cyclopentanedione 9 (98 mg, 1 mmol) in acetone (4 mL) and water (1 mL) NBS (214 mg,1.2 mmol) was added and the mixture was stirred for 16 h at room temperature. Water (4 mL) was then added, acetone was removed under reduced pressure, and the aqueous phase was extracted with CH2Cl2 (18 mL and 45 mL). The combined extracts were dried (Na2SO4) and concentrated. Flash chromatography (silica gel, heptanes/EtOAc 10:2) gave compound 1 as a white solid (158 mg, 89%)

References:

Paju, Anne;Kanger, T?nis;Müürisepp, Aleksander-Mati;Aid, Tiina;Pehk, T?nis;Lopp, Margus [Tetrahedron,2014,vol. 70,# 35,p. 5843 - 5848]