Iodine → 3-Iodobenzaldehyde diethyl acetal

To a stirred -78° C. solution of 3-bromobenzaldehyde diethyl acetal, prepared as in step 1, (1.0 g, 3.8 mmol) in THF (10 mL) was added n-butyllithium (1.7 mL, 4.25 mmol, 2.5M in hexanes). The cold reaction mixture was stirred 0.5 hours followed by the addition of a THF (5 mL) solution of iodine (1.09 g, 4.25 mmol). The ice bath was removed and the reaction allowed to warm to ambient temperature. Saturated NH4Cl was added and the mixture diluted with hexanes. The organic layer was washed with brine, dried (MgSO4) and concentrated under reduced pressure to give a residue which was purified by column chromatography on silica gel eluting with 5% ethyl acetate-hexanes to afford 1.0 g of 3-iodobenzaldehyde diethyl acetal.

1. customThe cold reaction mixture
2. customThe ice bath was removed
3. additionSaturated NH4Cl was added
4. additionthe mixture diluted with hexanes
5. washThe organic layer was washed with brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated under reduced pressure
8. customto give a residue which
9. customwas purified by column chromatography on silica gel eluting with 5% ethyl acetate-hexanes

ORD record

ord-6efb15823f2049789cc24967e559a6a3

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05616596