3-Bromophenol → 1-Bromo-3-(2,2-diethoxyethoxy)benzene

A solution of 10 gm (57.8 mMol) 3-bromophenol in 25 mL dimethylformamide was added dropwise to a mixture of 2.8 gm (70 mMol) sodium hydride (60% suspension in mineral oil) in 30 mL dimethylformamide. The reaction mixture was stirred for one hour after the addition was complete. To the reaction mixture was then added 9.7 mL (64.5 mMol) bromoacetaldehyde diethyl acetal and the resulting mixture was stirred at 153° C. for 2 hours. The reaction mixture was then allowed to cool to room temperature and was diluted with 300 mL diethyl ether. This mixture was then washed with two 150 ml portions of water, washed with 50 mL saturated aqueous sodium chloride, dried over magesium sulfate and concentrated under reduced pressure to provide about 17 gm of the desired compound.

1. additionafter the addition
2. stirringthe resulting mixture was stirred at 153° C. for 2 hours
3. washThis mixture was then washed with two 150 ml portions of water
4. washwashed with 50 mL saturated aqueous sodium chloride
5. dry with materialdried over magesium sulfate
6. concentrationconcentrated under reduced pressure

ORD record

ord-a2ff8467d08d4465b2ff2fc3c6b532fd

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07045545B1