4-(Trifluoromethyl)phenol → HCID 178506222, compound

HRID 1433201Notes

Reaction equation

C(OC([N:8]1[C:12]2[CH:13]=[CH:14][C:15]([Br:17])=[CH:16][C:11]=2[N:10]=[C:9]1[C:18](Cl)([F:20])[F:19])=O)(C)(C)C.[F:22][C:23]([F:32])([F:31])[C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1.C(N(CC)C(C)C)(C)C>>[Br:17][C:15]1[CH:14]=[CH:13][C:12]2[NH:8][C:9]([C:18]([F:19])([F:20])[O:30][C:27]3[CH:28]=[CH:29][C:24]([C:23]([F:22])([F:31])[F:32])=[CH:25][CH:26]=3)=[N:10][C:11]=2[CH:16]=1

Participants

Reactant 3

HCID 678744-(Trifluoromethyl)phenol

HCID 81531Diisopropylethylamine

HCID 57934951HCID 57934951, compound

Product 1

HCID 178506222HCID 178506222, compoundYield 54.4%

Conditions

Temperature: 85 °C

Procedure

A mixture of 5-bromo-2-(chloro-difluoro-methyl)-benzoimidazole-1-carboxylic acid tert-butyl ester (1.00 g, 2.62 mmol), 4-trifluoromethyl-phenol (0.42 g, 3.93 mmol), and N,N-diisopropylethylamine (0.6 mL, 3.44 mmol) was heated to 85° C. for 14 hours. The crude product was purified by chromatography (silica, hexanes: EtOAc, 4:1) to afford the title compound as a yellow oil (0.58 g, 54%).

Workup

customThe crude product was purified by chromatography (silica, hexanes: EtOAc, 4:1)

Sources & evidence

ORD record: ord-4384b3cf1373407b97ac49047336f8c0
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612211B2

Reaction notes

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