Methanol → Methyl 5-(bromomethyl)thiazole-4-carboxylate

To a mixture of 5-methylthiazole-4-carboxylic acid 3a (0.50 g, 3.49 mmol) in MeOH (15 mL) at 0° C. was added SOCl2 (0.51 mL, 6.99 mmol). The reaction was warmed up to room temperature and then heated to reflux for 8 h. The reaction mixture was cooled to room temperature and concentrated. The residue was dissolved in CH2Cl2 and washed with aq. NaHCO3. The organic solution was dried over Na2SO4 and concentrated. A portion of the resulting mixture (250 mg, 1.59 mmol) was heated to reflux in CCl4 (15 mL) with NBS (311 mg, 1.75 mmol) and benzoyl peroxide (38.5 mg, 0.159 mmol) for 3 h. The reaction mixture was concentrated and purification by flash column chromatography (silica gel, 30% EtOAc/heptane) gave compound 3b (250 mg).

1. temperatureheated
2. temperatureto reflux for 8 h
3. temperatureThe reaction mixture was cooled to room temperature
4. concentrationconcentrated
5. dissolutionThe residue was dissolved in CH2Cl2
6. washwashed with aq. NaHCO3
7. dry with materialThe organic solution was dried over Na2SO4
8. concentrationconcentrated
9. concentrationThe reaction mixture was concentrated
10. custompurification by flash column chromatography (silica gel, 30% EtOAc/heptane)

ORD record

ord-c2ae47cd7eab44fdbe243cffc793f3cf

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08759533B2