3-Bromophenol → 1-Bromo-3-(methoxymethoxy)benzene

Temperature

0 °C

To a solution of 31.4 g (183.3 mmol) of 3-Bromo-phenol in 450 mL of dried acetonitrile a dispersion of 12 g (274.9 mmol) of sodium hydride (55% in oil) was added portionwise at 0° C. The mixture was then allowed to agitate at 0° C. for 3 hours. A solution of 25 g (210.8 mmol) of chloromethyl ethyl ether in 30 mL of acetonitrile was added dropwise, and the mixture was allowed to agitate overnight at room temperature (20-30° C.). The reaction mixture was then filtered and the filter cake was washed with a small amount of acetone. The combined filtrates were evaporated. This gave 32.3 g of 1-Bromo-3-methoxymethoxy-benzene. The resulting crude product was used in the next step without further purification.

1. stirringto agitate overnight at room temperature (20-30° C.)
2. filtrationThe reaction mixture was then filtered
3. washthe filter cake was washed with a small amount of acetone
4. customThe combined filtrates were evaporated
5. customThe resulting crude product was used in the next step without further purification

ORD record

ord-ecb2543506934eff8983111158611306

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07491244B2