p-Fluoronitrobenzene → 4-[4-(trifluoromethoxy)phenoxy]aniline

HRID 1597430Notes

Reaction equation

HRID 1597430 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][CH:3]=1.[F:11][C:12]([F:22])([F:21])[O:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.CC([O-])(C)C.[K+].[H][H]>[Pd]>[F:11][C:12]([F:21])([F:22])[O:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:2]2[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 70015p-(Trifluoromethoxy)phenolHCID 23665647Potassium tert-butoxideHCID 178418361HCID 178418361, compound

Product 1

HCID 116661924-[4-(trifluoromethoxy)phenoxy]aniline

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Reaction of 4-fluoro-nitrobenzene with 4-trifluoromethoxyphenol in the presence of KOtBu as described in Example 74A, followed by reduction of the nitro group (hydrogen, 10% Pd/C) gave 4-(4-trifluoromethoxyphenoxy)-aniline. The aniline (4.58 g, 17 mmol) was dissolved in conc. HCl (3.1 mL) and ice (4.5 g) cooled to −5 C., then treated with a solution of NaNO2 (1.17 g, 17 mmol) in water (7mL) which was added dropwise. The cold soltion was added to an aqueous (7 mL) solution of potassium xanthate (5.46 g, 34 mmol) and the resulting mixture was heated at 70 C for 2 h, then allowed to cool to rt and partitioned between EtOAc and water. The organic extract was dried (MgSO4), filt ered and concentrated to give the title compound

Sources & evidence

ORD record
ord-187d79ebbc23405bb705c12980ff043b
Source dataset
uspto-grants-2001_09
Patent number
US06294573B1

Reaction notes

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