Methyl iodide → 3-Bromo-2-methoxybenzaldehyde

To a 500 mL two-neck round flask charged with 3-bromo-2-hydroxybenzaldehyde (D98) (13 g, 64.7 mmol) was added DMF (300 mL). Then K2CO3 (17.88 g, 129 mmol) was added, followed with methyl iodide (18.36 g, 129 mmol) at room temperature. The resulted mixture was stirred at room temperature. The mixture was stirred at room temperature overnight. The mixture was filtered through celite and washed with EtOAc. The resulted filtration was concentrated under reduced pressure. The residue was dissolved in EtOAc (250 mL), and washed with water (100 mL), 1N HCl (100 mL×2) and brine (100 mL×2). The organic layers was dried with sodium sulphate and concentrated. The residue was purified with ISCO column chromatography to afford 3-bromo-2-(methyloxy)benzaldehyde (D99) (4.05 g) as pale yellow oil. MS (ES): C8H7BrO2 requires 213.9. found 215.0 (M+H+).

1. stirringThe mixture was stirred at room temperature overnight
2. filtrationThe mixture was filtered through celite
3. washwashed with EtOAc
4. filtrationThe resulted filtration
5. concentrationwas concentrated under reduced pressure
6. dissolutionThe residue was dissolved in EtOAc (250 mL)
7. washwashed with water (100 mL), 1N HCl (100 mL×2) and brine (100 mL×2)
8. dry with materialThe organic layers was dried with sodium sulphate
9. concentrationconcentrated
10. customThe residue was purified with ISCO column chromatography

ORD record

ord-331de00e07294217b200e17c59d274e8

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08389508B2