4-Nitrophenol → 2-Chloro-4-(4-nitrophenyloxy)-5-trifluoromethylpyrimidine

HRID 1427378Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].[Cl:13][C:14]1[N:19]=[C:18]([Cl:20])[C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][N:15]=1>C(O)C>[Cl:13][C:14]1[N:15]=[C:16]([O:10][C:7]2[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[C:17]([C:21]([F:24])([F:22])[F:23])=[CH:18][N:19]=1.[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:14]2[N:19]=[C:18]([Cl:20])[C:17]([C:21]([F:23])([F:24])[F:22])=[CH:16][N:15]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: -15 °C

Procedure

Yet alternatively, 0.67 g 4-nitrophenol are dissolved in 5 mL ethanol. 4.6 mL of 1 M aqueous sodium hydroxide solution are added. The mixture is cooled to −15° C. A solution of 1.0 g 2,4-dichloro-5-trifluoromethylpyrimidine in 2 mL ethanol is added at −15° C. in portions. The suspension is stirred for 1.5 hours at −15° C. to −10° C. and then warmed up to 20° C. during 3 hours. The suspension is stirred 16 hours at 20° C. The precipitate is filtered and washed with a 1:1-mixture of methanol and purified water. The product is dried in a vacuum drying oven. 1.3 g (88% of theory) of title product is obtained with a regioisomeric purity of 88:12 (2-chloro-4-(4-nitrophenyloxy)-5-trifluoromethylpyrimidine:2-(4-nitrophenyloxy)-4-chloro-5-trifluoromethylpyrimidine).

Workup

temperaturewarmed up to 20° C. during 3 hours
stirringThe suspension is stirred 16 hours at 20° C
filtrationThe precipitate is filtered
washwashed with a 1
custom1-mixture of methanol and purified water
customThe product is dried in a vacuum
customdrying oven

Sources & evidence

ORD record: ord-a9f7a937f5ae493d9fdf8944e490a482
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933227B2

Reaction notes

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