Toluene → Azoxystrobin

HRID 1859226

Reaction equation

HRID 1859226 reaction equation
[OH-].[K+].[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[OH:11])#[N:4].Cl[C:13]1[N:18]=[CH:17][N:16]=[C:15]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2/[C:26](=[CH:31]\[O:32][CH3:33])/[C:27]([O:29][CH3:30])=[O:28])[CH:14]=1.C1(C)C=CC=CC=1>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][C:13]1[N:18]=[CH:17][N:16]=[C:15]([O:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2/[C:26](=[CH:31]\[O:32][CH3:33])/[C:27]([O:29][CH3:30])=[O:28])[CH:14]=1)#[N:4]

Participants

7

Reactant 4

HCID 1140TolueneHCID 119072-HydroxybenzonitrileHCID 14797Potassium HydroxideHCID 11782200Methyl (2E)-2-(2-((6-chloropyrimidin-4-yl)oxy)phenyl)-3-methoxyprop-2-enoate

Product 1

HCID 3034285AzoxystrobinYield 72.6%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
97.5 °C

Procedure

To a solution of potassium hydroxide (12.0 g) in water (10 g) was added, with stirring, 2-cyanophenol (13.2 g). The resulting solution was added, over 5 minutes, to (E)-methyl 2-[2-(6-chloropyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (32.8 g) at 95° C. and the temperature was maintained at 95-100° C. during the addition. Tetrabutylammonium bromide (1.5 g) was then added and the resulting mixture stirred for 20 hours at 95-100° C. The reaction mixture was mixed with water and toluene and the organic layer separated. The toluene solution contained (E)-methyl 2-[2-(6-(2-cyanophenoxy)pyrimidin-4-yloxy)phenyl]-3-methoxypropenoate (72.6% yield).

Workup

  1. stirringthe resulting mixture stirred for 20 hours at 95-100° C
  2. customthe organic layer separated

Sources & evidence

ORD record
ord-4fb607da5dfd48be86411394b2791740
Source dataset
uspto-grants-2000_11
Patent number
US06153750

Linked notes

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