Iodine → tert-Butyl 4-amino-3-iodobenzylcarbamate

To a mixture of (4-amino-benzyl)-carbamic acid tert-butyl ester (4.8 g, 21.6 mmol) and calcium carbonate (2.7 g, 27 mmol) in methanol (60 mL) was added iodine (5.5 g, 21.6 mmol) in portions. The mixture was heated at reflux overnight and then concentrated in vacuo to give a dark brown residue, which was partitioned between ethyl acetate and saturated sodium bisulfite solution. The organic phase was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give a residue, which was purified by chromatography (5%-20% ethyl acetate in hexanes) to give 3.5 g (47%) of the desired product as a brown semi-solid. MS(APCI+): m/z 349.1 (MH+).

1. temperatureThe mixture was heated
2. temperatureat reflux overnight
3. concentrationconcentrated in vacuo
4. customto give a dark brown residue, which
5. customwas partitioned between ethyl acetate and saturated sodium bisulfite solution
6. washThe organic phase was washed with water and brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationThe filtrate was concentrated in vacuo
10. customto give a residue, which
11. customwas purified by chromatography (5%-20% ethyl acetate in hexanes)

ORD record

ord-0e25684666ea4fcb97dd193a43e2935f

Source dataset

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06951848B2