Methyl 4-(2-bromoethyl)benzoate → [4-(2-Bromoethyl)phenyl]methanol

Temperature

0 °C

To a suspension of LiAlH4 (4.5 mmol; 0.172 g) in anhydrous THF (5.0 ml) cooled to 0° C. was added dropwise a solution of methyl 4-(2-bromoethyl)benzenecarboxylate (1.0 g; 4.1 mmol) in anhydrous THF (10.0 ml). The reaction mixture was stirred for 5 minutes at room temperature and, after adding ice, was filtered through a Büchner filter. The solvent was removed under reduced pressure and the residue was extracted with ethyl acetate (3×100 ml). The combined organic phases were washed with saturated NaCl solution, dried over sodium sulfate and evaporated under reduced pressure. 800 mg (82.6%) of pure product were thus obtained as an oil.

1. additionafter adding ice
2. filtrationwas filtered through a Büchner
3. filtrationfilter
4. customThe solvent was removed under reduced pressure
5. extractionthe residue was extracted with ethyl acetate (3×100 ml)
6. washThe combined organic phases were washed with saturated NaCl solution
7. dry with materialdried over sodium sulfate
8. customevaporated under reduced pressure

ORD record

ord-edc8e15a681a46709d415a097f36b4ae

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08686147B2