Diisobutylaluminumhydride → 2-(2-Bromo-4-fluorophenoxy)propionaldehyde

Temperature

-78 °C

A solution of 19.4 gm (66.7 mMol) ethyl 2-(2-bromo-4-fluorophenoxy)propionate in 400 mL toluene was cooled to −78° C. at which point 100 mL (100 mMol) diisobutylaluminum hydride (1 M in toluene) were added dropwise over 35 minutes. The reaction mixture was stirred at −78° C. for an additional 20 minutes after the addition was complete and then the reaction was quenched by the addition of methanol. The reaction mixture was warmed to room temperature and then treated with saturated aqueous sodium potassium carbonate. The mixture was stirred for 30 minutes and was then extracted well with ethyl acetate. The organic phases were combined, dried over sodium sulfate, and concentrated under reduced pressure to provide 16.9 gm of crude desired compound.

1. additionwere added dropwise over 35 minutes
2. additionafter the addition
3. customthe reaction was quenched by the addition of methanol
4. temperatureThe reaction mixture was warmed to room temperature
5. additiontreated with saturated aqueous sodium potassium carbonate
6. stirringThe mixture was stirred for 30 minutes
7. extractionwas then extracted well with ethyl acetate
8. dry with materialdried over sodium sulfate
9. concentrationconcentrated under reduced pressure

ORD record

ord-40821cd678f541069ddefc36a62680fe

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07045545B1