Tetrahydrofuran → (5-(Benzyloxy)-2-bromo-3-methylphenyl)methanol

Temperature

-78 °C

A solution of methyl 5-(benzyloxy)-2-bromobenzoate (1.08 g, 3.36 mmol) in anhydrous THF (7 mL) was made before cooling the reaction mixture in a −78° C. bath. Reaction mixture was then treated, dropwise, with LiAlD4 (1 M solution in THF; 3.7 mL, 3.7 mmol) and allowed to stir for 21 h. before the reaction mixture was warmed to room temperature and quenched with 1N HCl to adjust pH 7 before addition of 10 mL of EtOAc. The organic layer was separated and the aqueous layer was further extracted with equal volume of EtOAc before the organic layers were combined and dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure. The residue was purified by silica gel column using Combiflash to give (5-(benzyloxy)-2-bromo-3-methylphenyl)methanol −d2 (2.00 g, 86%).

1. customReaction mixture
2. additionwas then treated
3. temperaturewas warmed to room temperature
4. customquenched with 1N HCl
5. additionbefore addition of 10 mL of EtOAc
6. customThe organic layer was separated
7. extractionthe aqueous layer was further extracted with equal volume of EtOAc before the organic layers
8. dry with materialdried over anhydrous Na2SO4
9. filtrationfiltered
10. customThe solvent was removed under reduced pressure
11. customThe residue was purified by silica gel column

ORD record

ord-6cf3514d9edc47d78f00b66c0e61fea9

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716478B2