Iodine → 2-Iodo-1-benzofuran

Temperature

-10 °C

To a solution of benzofuran (3.0 g, 25.4 mmol) in tetrahydrofuran (36 mL) at about −78° C. was added a 2.5M solution of n-butyllithium in hexanes (10.2 mL, 25.4 mmol). The solution was allowed to warm to about −10° C. and was stirred for about 2 hours. Iodine (6.41 g, 25.4 mmol) was added gradually and the mixture was stirred at about −10° C. for about 30 min. The solution was allowed to warm to room temperature, was quenched by the addition of aqueous ammonium chloride, and was extracted with diethyl ether. The combined organic extracts were washed with aqueous sodium bisulfite and brine, dried (MgSO4), filtered and concentrated under vacuum. The resulting oil was distilled (b.p. 90° C./1.05 mm Hg) to provide Example 651. 1H NMR (300 MHz, CDCl3): δ 6.93 (s, 1H), 7.20 (m, 2H), 7.48 (m, 2H).

1. stirringthe mixture was stirred at about −10° C. for about 30 min
2. temperatureto warm to room temperature
3. customwas quenched by the addition of aqueous ammonium chloride
4. extractionwas extracted with diethyl ether
5. washThe combined organic extracts were washed with aqueous sodium bisulfite and brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated under vacuum
9. distillationThe resulting oil was distilled (b.p. 90° C./1.05 mm Hg)
10. customto provide Example 651

ORD record

ord-f694577364274b7b8c409de653b44698

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07468371B2