Hydrochloric Acid → 1-(2-Bromothiazol-5-yl)ethanol

Temperature

0 °C

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of commercially available 2-bromo-thiazole-5-carbaldehyde (1.80 g, 9.37 mmol) in CH2Cl2 (70.0 mL) was treated at 0° C. with trimethylaluminum (46.0 mL of a 1M solution in heptane, 46 mmol). The reaction mixture was then stirred at 0° C. for 45 min. CH2Cl2 (100.0 mL) followed by sat. aq. NH4Cl (100 mL) was then added. The mixture was then treated with 1N HCl (50 mL) and the aq. layer was extracted with CH2Cl2 (150 mL). The combined org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow oil. TLC:rf (1:2 hept-EA)=0.40. LC-MS-conditions 02: tR=0.70 min; [M+AcCN+H]+=249.17.

1. additionwas then added
2. extractionthe aq. layer was extracted with CH2Cl2 (150 mL)
3. dry with materialextracts were dried over MgSO4
4. filtrationfiltered
5. customthe solvents were removed under reduced pressure

ORD record

ord-c67d3271e4b54c058774ed5ec8e8fc63

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08536209B2