Reaktion #497714

Reaktionsgleichung

Bromine

product

dicyclopropyl(1,3-thiazol-2-yl)methanol

NaOAc

→

(5-bromo-1,3-thiazol-2-yl)(dicyclopropyl)methanol

Ausbeute 57.1%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched with brine
2. 2
   Extraktionthe aqueous layer was extracted with ethyl acetate (3×)
3. 3
   WaschenThe combined organics were washed with brine
4. 4
   Trocknendried (sodium sulfate)
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe residue was purified by chromatography on silica gel (0-100% ethyl acetate in hexanes)

Vorschrift

Bromine (0.271 mL, 5.26 mmol) was added dropwise to a stirred mixture of the product of Step 1 (411 mg, 2.10 mmol) and NaOAc (863 mg, 10.5 mmol) in acetic acid (9.17 mL) and the mixture was stirred at room temperature for 4 h. The reaction was quenched with brine and the aqueous layer was extracted with ethyl acetate (3×). The combined organics were washed with brine, dried (sodium sulfate), filtered, and concentrated. The residue was purified by chromatography on silica gel (0-100% ethyl acetate in hexanes) to give (5-bromo-1,3-thiazol-2-yl)(dicyclopropyl)methanol (329 mg, 1.20 mmol, 57% yield) as an off-white solid. MS APCI: [M-OH]+ m/z 255.9

Quelle