2-Bromo-1,3-thiazole-5-carbaldehyde → 1-(2-Bromothiazol-5-yl)ethanol

To a 0° C. solution of 2-bromo-5-formylthiazole (100.6 mg, 0.524 mmol) in THF (5 mL) was added MeMgBr (175 μL of a 3M solution in Et2O, 0.524 mmol). After 30 minutes, additional MeMgBr (50 μL of a 3M solution in Et2O, 0.150 mmol) was added. After 30 more minutes, the reaction was quenched by pouring into saturated NH4Cl (20 mL). The mixture was extracted with EtOAc (50 mL) and the organic layer was washed with water and brine (25 mL each). The organic layer was dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography (0 to 80% EtOAc/hexanes) afforded 1-(2-bromo-1,3-thiazol-5-yl)ethanol. Rf=0.13 (25% EtOAc/hexanes). LCMS=210.0 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.40 (s, 1H), 5.12 (q, J=6.4 Hz, 1H), 1.59 (d, J=6.4 Hz, 3H).

1. customAfter 30 more minutes, the reaction was quenched
2. additionby pouring into saturated NH4Cl (20 mL)
3. extractionThe mixture was extracted with EtOAc (50 mL)
4. washthe organic layer was washed with water and brine (25 mL each)
5. dry with materialThe organic layer was dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customPurification of the residue by flash chromatography (0 to 80% EtOAc/hexanes)

ORD record

ord-e30e63b33e614b7bb359faf56d0576b4

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735435B2