Dimethyl Sulfoxide → Methyl 4-formyl-3-methoxybenzoate

To a stirred solution of 4-bromo-3-methoxybenzoic acid (15.0 g, 58 mmol) in DMSO (150 mL) was added NaHCO3 (20.0 g, 230 mmol). This was heated to 80° C. for 18 hours. The reaction was then cooled to room temperature and the solvent removed under reduced pressure. The crude reaction mixture was then dissolved in DCM (200 mL) and washed with 1N HCl (100 mL), water (100 mL), NaCl (sat.) (100 mL), dried over MgSO4 and then filtered. The solvent was removed under reduced pressure. The crude material was sufficiently pure to use without further purification. The title intermediate was obtained in 79% yield (8.9 g, 45.8 mmol).

1. temperatureThe reaction was then cooled to room temperature
2. customthe solvent removed under reduced pressure
3. customThe crude reaction mixture
4. washwashed with 1N HCl (100 mL), water (100 mL), NaCl (sat.) (100 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customThe solvent was removed under reduced pressure
8. customto use without further purification

ORD record

ord-f1c755adcb0f453e8971ffdb5f6101a3

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07728144B2