Methyl 2-Bromo-5-chlorobenzoate → (2-Bromo-5-chlorophenyl)methanol

A solution of methyl 2-bromo-5-chlorobenzoate (4.9 g, 19.64 mmol) in THF (50 mL) was cooled to 0° C. and treated with the dropwise addition of LAH (1.0M in THF) (20.62 mL, 20.62 mmol), causing a mild exotherm and gas evolution. The mixture was allowed to warm to room temperature and stirred for 3 hours. The reaction was quenched using the Steinhardt procedure (see Fieser & Fieser, Reagents for Organic Synthesis, p. 584). The resulting precipitate was removed by filtration and washed with ethyl acetate. The combined filtrates were concentrated in-vacuo to yield a colorless oil which solidified upon standing. The residue was purified over a 330 g silica gel column via ISCO, eluting with a 10-100% EtOAc/Hexanes gradient over 30 minutes, to yield the title compound (2.04 g, 47% yield) as a colorless powder.

1. customThe reaction was quenched
2. customthe Steinhardt procedure (see Fieser & Fieser, Reagents for Organic Synthesis, p. 584)
3. customThe resulting precipitate was removed by filtration
4. washwashed with ethyl acetate
5. concentrationThe combined filtrates were concentrated in-vacuo
6. customto yield a colorless oil which
7. customThe residue was purified over a 330 g silica gel column via ISCO
8. washeluting with a 10-100% EtOAc/Hexanes
9. waitgradient over 30 minutes

ORD record

ord-5076ea7eaf204fd596e60acca2019215

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07985861B2