Iodine → 1-(2-Iodophenyl)cyclopropane-1-carboxylic acid

A solution of 1-phenyl-1-cyclopropanecarboxylic acid (2.00 g, 12.3 mmol), Pd(OAc)2 (0.138 g, 0.617 mmol), iodine (2.34 g, 9.24 mmol) and (diacetoxyiodo)benzene (2.97 g, 9.24 mmol) in DMF (10 mL) was stirred at 60° C. for 18 hours covered aluminium foil. Additional iodine (2.34 g, 9.24 mmol) and (diacetoxyiodo)benzene (2.97 g, 9.24 mmol) were added and stirring was continued at 60° C. for a further 8 hours. A final addition of iodine (2.34 g, 9.24 mmol) and (diacetoxyiodo)benzene (2.97 g, 9.24 mmol) was performed and stirring was continued at 60° C. for a further 16 hours. The resulting mixture was partitioned between EtOAc and water and the aqueous phase was extracted several times with EtOAc. The combined organic extracts were washed with a 10% aqueous solution of sodium metabisulfate (3×30 mL), 10% aqueous citric acid (2×30 mL), water, brine, dried (MgSO4), filtered and evaporated. The residue was purified using silica gel column chromatography (CombiFlash Rf, 80 g SiO2 Cartridge, 30-40% EtOAc in cyclohexane) to give the title compound I10 as a cream solid (3.11 g, 87%); 1H NMR (300 MHz, CDCl3) δ 7.88 (d, J=8.0 Hz, 1H), 7.28-7.35 (m 2H), 6.97-7.03 (m, 1H), 2.13 (brs, 2H), 1.30 (brs, 2H).

1. stirringstirring
2. waitwas continued at 60° C. for a further 16 hours
3. customThe resulting mixture was partitioned between EtOAc and water
4. extractionthe aqueous phase was extracted several times with EtOAc
5. washThe combined organic extracts were washed with a 10% aqueous solution of sodium metabisulfate (3×30 mL), 10% aqueous citric acid (2×30 mL), water, brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customevaporated
9. customThe residue was purified

ORD record

ord-7a4ef0997ca14cbdb20d70bd9b459b24

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238644B2