Chloromethyl Methyl Ether → 1-Bromo-3-(methoxymethoxy)benzene

Temperature

0 °C

To a solution of 3-bromophenol (27.4 g, 158 mmol) in CH2Cl2 was added chloromethyl methyl ether (18 mL, 237 mmol). The reaction mixture was cooled to 0° C. and diisopropylethylamine (55 mL, 316 mmol) was added and the cold bath was removed. The reaction mixture was stirred for 3 hours at ambient temperature and then poured into 10% aqueous HCl. The layers were separated and the aqueous phase was extracted 4 times with CH2Cl2. The combined organic layers were washed once each with saturated aqueous NaHCO3, 15% aqueous NaOH, and brine, dried over MgSO4, filtered, and concentrated in vacuo to provide 3-methyloxymethoxy-bromobenzene as a yellow oil.

1. customthe cold bath was removed
2. additionpoured into 10% aqueous HCl
3. customThe layers were separated
4. extractionthe aqueous phase was extracted 4 times with CH2Cl2
5. washThe combined organic layers were washed once each with saturated aqueous NaHCO3, 15% aqueous NaOH, and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-303570a8140c45fcac4a4226fe71200b

Source dataset

uspto-grants-1994_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05354865