2-(Benzyloxy)-3-bromobenzaldehyde → (2-(Benzyloxy)-3-bromophenyl)(phenyl)methanol

A solution of 8 (8.6 g, 29.55 mmol, 1.0 equiv) in THF (220 mL) was cooled to ˜10° C. and 1M PhMgBr in THF (45 mL, 45 mmol, 1.5 equiv) was added slowly via syringe at <10° C. A pale yellow color initially developed that changed to light blue then back to pale yellow. The mixture was allowed to warm to room temperature and stirred 2 hr. The mixture was recooled to ˜0° C. and quenched by addition of saturated NH4Cl solution (100 mL). The mixture was partitioned between EtOAc (300 mL) and H2O (25 mL). The organic phase was washed with brine (200 mL), dried over Na2SO4, filtered and the solution concentrated under reduced pressure to give a yellow oil. The crude product was absorbed onto silica gel using DCM and dry-loaded on a column of silica gel (100 g) packed in heptanes. The column was eluted with heptanes (1 L), 5% EtOAc/heptanes (1 L) and 10% EtOAc/heptanes (2 L). Product fractions were concentrated under reduced pressure to give 8.7 g (80%) of 9 as a nearly colorless oil.

1. customwas recooled to ˜0° C.
2. customquenched by addition of saturated NH4Cl solution (100 mL)
3. customThe mixture was partitioned between EtOAc (300 mL) and H2O (25 mL)
4. washThe organic phase was washed with brine (200 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationthe solution concentrated under reduced pressure
8. customto give a yellow oil
9. customThe crude product was absorbed onto silica gel
10. washThe column was eluted with heptanes (1 L), 5% EtOAc/heptanes (1 L) and 10% EtOAc/heptanes (2 L)
11. concentrationProduct fractions were concentrated under reduced pressure

ORD record

ord-8d520729888746c89b0f0e89fac9d252

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541521B2