Imidazole → 1,3-Dichloro-2-{2-[4-(iodomethyl)phenoxy]ethoxy}-5-methylbenzene

To a solution of triphenylphosphine (1.2 eq.) in dichloromethane (0.09 M) was added iodine (1.2 eq.) and the resulting reddish-orange mixture was stirred at RT for 15 min. At 0° C., a dichloromethane solution (0.1 M) of {4-[2-(2,6-dichloro-4-methylphenoxy)ethyoxy]phenyl}methanol prepared in the previous step (1 eq.) and imidazole (3 eq.) was then added dropwise over 15 min. The resulting orange-yellow suspension was stirred at 0° C. for 1 h and then at RT for 15 min. The reaction was quenched with 10% (w/w) aq. NaHSO3 and extracted with ether. The organic extracts were combined, washed with brine, dried over MgSO4, filtered and the filtrate concentrated in vacuo. The resulting residue was triturated in a 10:1 (v/v) Hex:ether solution and filtered through a pad of SiO2. The filtrate was concentrated in vacuo to afford the title compound as a white solid.

1. additionwas then added dropwise over 15 min
2. stirringThe resulting orange-yellow suspension was stirred at 0° C. for 1 h
3. waitat RT for 15 min
4. customThe reaction was quenched with 10% (w/w) aq. NaHSO3
5. extractionextracted with ether
6. washwashed with brine
7. dry with materialdried over MgSO4
8. filtrationfiltered
9. concentrationthe filtrate concentrated in vacuo
10. customThe resulting residue was triturated in a 10:1 (v/v)
11. filtration:ether solution and filtered through a pad of SiO2
12. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-701387b760a14f228f5e8d7137e367eb

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063105B2