Methanol → Methyl 3-bromothiophene-2-carboxylate

3-Bromothiophene-2-carboxylic acid (5.0 g, 24 mmol, 1 eq.) was dissolved in MeOH (100 mL) and the mixture was degassed and purged with nitrogen (2×). SOCl2 (15 mL, 0.2 mol, 8.3 eq.) was added dropwise and the resulting mixture was stirred overnight at room temperature. The mixture was then concentrated and DCM (150 mL) was added. Saturated NaHCO3 (20 mL) was added, and the resulting mixture was stirred at room temperature for 15 minutes. The organic layer was washed with saturated NaHCO3 (20 mL), water (20 mL), and saturated aqueous NaCl (20 mL), then dried over Na2SO4, filtered and concentrated to yield 3-bromothiophene-2-carboxylic acid methyl ester (4.0 g) as a yellow solid.

1. customthe mixture was degassed
2. custompurged with nitrogen (2×)
3. concentrationThe mixture was then concentrated
4. additionDCM (150 mL) was added
5. additionSaturated NaHCO3 (20 mL) was added
6. stirringthe resulting mixture was stirred at room temperature for 15 minutes
7. washThe organic layer was washed with saturated NaHCO3 (20 mL), water (20 mL), and saturated aqueous NaCl (20 mL)
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated

ORD-Eintrag

ord-80167fa325ac4c73b8b6b32d36edcb90

Quelldatensatz

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08530663B2