Dimethylformamide → 2,6-Dichloro-4-iodobenzaldehyde

To a stirred solution of 1,3-dichloro-5-iodobenzene (4.0 g, 14.6 mmol) in THF (30 mL), LDA (2.0 M in THF/heptane/ethylbenzene, 9.6 mL, 16.9 mmol) was added dropwise at −78° C. and stirred for 1 h at the same temperature. A solution of DMF (1.7 mL, 22.0 mmol) in THF (5 mL) was added slowly at −78° C. and stirred for 3 h. The reaction mixture was quenched with saturated NH4Cl (50 mL) and extracted with EtOAc (2×30 mL). The combined organic layers were washed with water (50 mL), brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, 20% EtOAc/hexane as eluent) to afford compound A35-1 (1.4 g, 32%) as colorless oil.

1. stirringstirred for 3 h
2. customThe reaction mixture was quenched with saturated NH4Cl (50 mL)
3. extractionextracted with EtOAc (2×30 mL)
4. washThe combined organic layers were washed with water (50 mL), brine (50 mL)
5. dry with materialdried over anhydrous Na2SO4
6. concentrationconcentrated under reduced pressure
7. customThe crude product was purified by column chromatography (silica gel, 20% EtOAc/hexane as eluent)
8. customto afford compound A35-1 (1.4 g, 32%) as colorless oil

ORD record

ord-ddb15e2f25b2446db4997231cf1ec64c

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365522B2