Aluminium lithium hydride → 3-Bromo-2-methylbenzaldehyde

Temperature

-78 °C

Lithium aluminum hydride (201 mg, 5.31 mmol) was added in one portion to a −78° C. solution of 3-bromo-N-methoxy-2,N-dimethyl-benzamide ((Example 6: step b) 1.1 g, 4.24 mmol) in THF (25 mL). After stirring for 1 h at −78° C., the hydride reagent was quenched with EtOAc (10 mL), and the solution was slowly poured into a vigorously stirred mixture of citric acid (10%, 30 mL) and EtOAc (50 mL). After separating the layers, the organic layer was washed with NaHCO3 (3×20 mL), water (20 mL), and brine (30 mL). The solution was dried (sodium sulfate) and the solvent was removed in vacuo, giving the title compound (813 mg, 96%) as a colorless oil which was used without further purification. 1H-NMR (CDCl3): δ 10.28 (s, 1H), 7.80 (m, 2H), 7.25 (m, 1H), 2.78 (s, 3H).

1. customthe hydride reagent was quenched with EtOAc (10 mL)
2. additionthe solution was slowly poured into a vigorously stirred mixture of citric acid (10%, 30 mL) and EtOAc (50 mL)
3. customAfter separating the layers
4. washthe organic layer was washed with NaHCO3 (3×20 mL), water (20 mL), and brine (30 mL)
5. dry with materialThe solution was dried (sodium sulfate)
6. customthe solvent was removed in vacuo

ORD record

ord-1b57af8e6ed64994a9415150e2b314cf

Source dataset

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07138530B2