p-(Trifluoromethoxy)phenol → HCID 66956539, compound

HRID 2066652Notes

Reaction equation

HRID 2066652 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.[F:16][C:17]([F:27])([F:26])[O:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1>>[Cl:1][C:2]1[N:3]([CH2:10][CH2:11][C:12]([CH3:15])([OH:13])[CH2:14][O:25][C:22]2[CH:21]=[CH:20][C:19]([O:18][C:17]([F:26])([F:27])[F:16])=[CH:24][CH:23]=2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1

Participants

3

Reactant 2

HCID 70015p-(Trifluoromethoxy)phenolHCID 86650547HCID 86650547, compound

Product 1

HCID 66956539HCID 66956539, compoundYield 77%

Procedure

Reaction of epoxide 140 with 4-trifluoromethoxyphenol as in Example 2AA at 82° C. for 10 h, followed by chromatography of the product on silica gel, eluting with CH2Cl2 (foreruns) and then with 0-2% EtOAc/CH2Cl2, gave 4-(2-chloro-4-nitro-1H-imidazol-1-yl)-2-methyl-1-[4-(trifluoromethoxy)phenoxy]-2-butanol (141) (77%) as a pale yellow oil; 1H NMR (CDCl3) δ 7.81 (s, 1H), 7.17 (br dd, J=9.1, 0.7 Hz, 2H), 6.90 (dt, J=9.2, 3.1 Hz, 2H), 4.29 (ddd, J=14.1, 9.5, 6.3 Hz, 1H), 4.24 (ddd, J=14.1, 9.6, 6.5 Hz, 1H), 3.85 (d, J=9.0 Hz, 1H), 3.82 (d, J=9.0 Hz, 1H), 2.23 (ddd, J=13.8, 9.3, 6.5 Hz, 1H), 2.21 (s, 1H), 1.40 (s, 3H); HRESIMS calcd for C15H16ClF3N3O5 m/z [M+H]+ 412.0697, 410.0725. found 412.0700, 410.0722.

Workup

  1. washeluting with CH2Cl2 (foreruns)

Sources & evidence

ORD record
ord-a095a58f7d80497094b08d6f5699c558
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

Loading…