18-Crown-6 → 3-Chloro-5-[(2-chloro-6-fluoro-3-methylphenyl)oxy]benzonitrile

HRID 1875126Notes

Reaction equation

HRID 1875126 reaction equation
C(O[K])(C)(C)C.[Cl:7][C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([F:15])[C:9]=1[OH:16].[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24](F)[CH:25]=1)[C:21]#[N:22].C1OCCOCCOCCOCCOCCOC1>CS(C)=O>[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=[C:24]([O:16][C:9]2[C:10]([F:15])=[CH:11][CH:12]=[C:13]([CH3:14])[C:8]=2[Cl:7])[CH:25]=1)[C:21]#[N:22]

Participants

6

Reactant 4

HCID 2855718-Crown-6HCID 27348413-Chloro-5-fluorobenzonitrileHCID 27736832-Chloro-6-fluoro-3-methylphenolHCID 178418922HCID 178418922, compound

Product 1

HCID 684836723-Chloro-5-[(2-chloro-6-fluoro-3-methylphenyl)oxy]benzonitrileYield 79.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The title compound was prepared as described herein using tBuOK (4.00 ml, 4.00 mmol), 2-chloro-6-fluoro-3-methylphenol (642 mg, 4.00 mmol), 3-chloro-5-fluorobenzonitrile (622 mg, 4.00 mmol) and 18-crown-6 (211 mg, 0.800 mmol) in dimethyl sulfoxide (16 ml) to give the title compound as a white solid (0.94 g, 79%). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.33 (1H, s) 7.12-7.19 (2H, m) 7.07 (1H, t, J=8.9 Hz) 6.98 (1H, s) 2.40 (3H, s). LCMS: m/z 294 (M−1).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-cc3c4422d20d44658b0acbe8155696a1
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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