Acetic Acid → 1-[3-(1,1-Difluoroethyl)phenyl]-1H-imidazole-4-methanol

HRID 397915Notes

Reaction equation

HRID 397915 reaction equation
[F:1][C:2]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])([F:4])[CH3:3].O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].C([O:46][CH2:47][CH3:48])(OCC)OCC.[N+:49]([CH2:52]C(OCC)=O)([O-])=O.[C:58](O)(=O)C>[Fe]>[F:1][C:2]([C:5]1[CH:6]=[C:7]([N:8]2[CH:58]=[C:48]([CH2:47][OH:46])[N:49]=[CH:52]2)[CH:9]=[CH:10][CH:11]=1)([F:4])[CH3:3]

Participants

7

Reactant 5

HCID 176Acetic Acid2×HCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetateHCID 180504Ceric ammonium nitrateHCID 234450923-(1,1-Difluoroethyl)aniline

Product 1

HCID 234451911-[3-(1,1-Difluoroethyl)phenyl]-1H-imidazole-4-methanol

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Following the general method described in example 293, 3-(1,1-difluoro-ethyl)-aniline [R. O. Neri, J. G. Topliss, Ger. Offen. (1972), DE 2130452 19721221 CAN 78:124310] was reacted with triethyl orthoformate, ethyl nitroacetate and acetic acid followed by treatment with triethyl orthoformate, iron and acetic acid and subsequent alkaline hydrolysis. The isolated acid was directly reduced according to example 264, by reaction with BH3 THF complex followed by hydrolytic workup and the title compound was obtained as a white crystalline solid. Mp. 104-108° C. (H2O), MS: m/e=238 (M+).

Workup

  1. customThe isolated acid was directly reduced according to example 264, by reaction with BH3 THF complex

Sources & evidence

ORD record
ord-0d4e59d30f634c5b9fc963f3fb5e1dee
Source dataset
uspto-grants-2003_08
Patent number
US06610723B2

Reaction notes

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