Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate → (2-Bromo-4-methylthiazol-5-yl)methanol

To a solution of ethyl 2-bromo-4-methylthiazole-5-carboxylate (7 g, 28 mmol) in EtOH (120 mL) and H2O (20 mL) was added portion-wise NaBH4 (3.2 g, 84 mmol). After the addition, the mixture was stirred at room temperature overnight. TLC (petroleum ether/EtOAc=5:1) showed the reaction was complete. The reaction mixture was carefully concentrated in vacuum. The residue was separated between EtOAc (50 mL) and H2O (50 mL). The inorganic layer was extracted with EtOAc (50 mL×2). The combined organic layers were washed with brine (100 mL), dried over sodium sulfate and concentrated in vacuum to give the title compound as a colorless oil (3.8 g, 65%).

1. additionAfter the addition
2. concentrationThe reaction mixture was carefully concentrated in vacuum
3. customThe residue was separated between EtOAc (50 mL) and H2O (50 mL)
4. extractionThe inorganic layer was extracted with EtOAc (50 mL×2)
5. washThe combined organic layers were washed with brine (100 mL)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated in vacuum

ORD record

ord-590aea3f72994e058e45a7beef361d23

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916593B2