Water → 4-Iodobenzamide

Crude 4-iodobenzoyl chloride (11.4 g, 42.7 mmol) in THF (75 mL), prepared above, was treated with ammonium hydroxide (5 mL) followed by water (40 mL) at ambient temperature. The reaction mixture was stirred for 3 hours and then partitioned between EtOAc (50 mL) and brine (50 mL). The phases were separated and the organic phase was washed with 10% aqueous NaHCO3 solution (30 mL) and brine (30 mL), dried over Na2SO4, and filtered. The filtrate volume was reduced until a white solid precipitated from solution. The white solid was collected by filtration and washed with diethyl ether to provide the desired product (10.2 g, 41.4 mmol, 97%).

1. custompartitioned between EtOAc (50 mL) and brine (50 mL)
2. customThe phases were separated
3. washthe organic phase was washed with 10% aqueous NaHCO3 solution (30 mL) and brine (30 mL)
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. customprecipitated from solution
7. filtrationThe white solid was collected by filtration
8. washwashed with diethyl ether

ORD record

ord-62f25909a56345ee80b2f5b04af20aa2

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06645968B2