Methanol → (2-Bromo-5-methylthiazol-4-yl)methanol

To a stirred solution of methyl 2-bromo-5-methyl-1,3-thiazole-4-carboxylate (2.89 g, 12.26 mmol, 1 eq.) in 120 ml dry THF cooled to 5° C., was added LiBH4 (2M in THF, 12.26 ml, 24.53 mmol, 2 eq.) followed by MeOH (0.994 ml, 24.53 mmol, 2 eq.). The reaction was allowed to warm to r.t. and was stirred for further 18 hrs. The reaction was quenched by addition of sat. aqueous NH4Cl and diluted with DCM. The aqueous layer was extracted with DCM, and the organic layers combined, dried over MgSO4 and concentrated. The residue was chromatographed on silica gel to (2-bromo-5-methyl-1,3-thiazol-4-yl)methanol (2.07 g, 77% yield) as a white solid.

1. customThe reaction was quenched by addition of sat. aqueous NH4Cl
2. additiondiluted with DCM
3. extractionThe aqueous layer was extracted with DCM
4. dry with materialdried over MgSO4
5. concentrationconcentrated

ORD record

ord-785689a942f14157a11f589f264ec4f6

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466176B2