Bromine → (5-Bromothiazol-2-yl)dicyclopropylmethanol

反応式

[Br:1]Br.[CH:3]1([C:6]([CH:13]2[CH2:15][CH2:14]2)([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)[OH:7])[CH2:5][CH2:4]1.CC([O-])=O.[Na+]>C(O)(=O)C>[Br:1][C:10]1[S:9][C:8]([C:6]([CH:3]2[CH2:5][CH2:4]2)([CH:13]2[CH2:14][CH2:15]2)[OH:7])=[N:12][CH:11]=1

参加物

実験手順

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