4-Iodophenol → HCID 66956448, compound

HRID 2066654Notes

Reaction equation

[Cl:1][C:2]1[N:3]([CH2:10][CH2:11][C:12]2([CH3:15])[CH2:14][O:13]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[I:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1>>[Cl:1][C:2]1[N:3]([CH2:10][CH2:11][C:12]([CH3:15])([OH:13])[CH2:14][O:23][C:20]2[CH:21]=[CH:22][C:17]([I:16])=[CH:18][CH:19]=2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

Reactant 2

HCID 108944-Iodophenol

HCID 86650547HCID 86650547, compound

Product 1

HCID 66956448HCID 66956448, compoundYield 81%

Procedure

Reaction of epoxide 140 (see Example 2B) with 4-iodophenol as in Example 2AA at 83° C. for 8 h, followed by chromatography of the product on silica gel, eluting with 0-2% EtOAc/CH2Cl2 (foreruns) and then with 5% EtOAc/CH2Cl2, gave 4-(2-chloro-4-nitro-1H-imidazol-1-yl)-1-(4-iodophenoxy)-2-methyl-2-butanol (143) (81%) as a cream solid: mp (CH2Cl2/pentane) 91-93° C.; 1H NMR (CDCl3) δ 7.80 (s, 1H), 7.59 (dt, J=8.9, 2.6 Hz, 1H), 6.69 (dt, J=8.9, 2.6 Hz, 1H), 4.28 (ddd, J=14.1, 9.6, 6.3 Hz, 1H), 4.23 (ddd, J=14.1, 9.4, 6.5 Hz, 1H), 3.82 (d, J=9.0 Hz, 1H), 3.79 (d, J=9.0 Hz, 1H), 2.22 (ddd, J=13.8, 9.2, 6.5 Hz, 1 H), 2.20 (s, 1H), 2.02 (ddd, J=13.8, 9.6, 6.6 Hz, 1H), 1.39 (s, 3H); HRESIMS calcd for C14H16ClIN3O4 m/z [M+H]+ 453.9840, 451.9869. found 453.9832, 451.9857.

Workup

washeluting with 0-2% EtOAc/CH2Cl2 (foreruns)

Sources & evidence

ORD record: ord-bf0ef6b6829c43ba97a45321e1a196bf
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293734B2

Reaction notes

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