Azobisisobutyronitrile → 2-Bromomethyl-5-(4-trifluoromethyl-phenyl)-pyrimidine

HRID 1242395Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)=[CH:4][N:3]=1.[Br:18]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:12][CH:13]=2)=[CH:6][N:7]=1

Participants

Conditions

Temperature: 75 °C

Procedure

0.31 g (1.3 mmol) of 2-methyl-5-(4-trifluoromethyl-phenyl)-pyrimidine, 0.255 g (1.43 mmol) of N-bromosuccinimide and 0.15 g (0.91 mmol) of 2,2′-azobis-(2-methyl-propionitril) were dissolved in 5 ml of carbon tetrachloride and the mixture was stirred at 75° C. Two portions of 0.13 g (0.73 mmol) of N-bromosuccinimide and of 0.075 g (0.046 mmol) of 2,2′-azobis-(2-methyl-propionitril) were added to the reaction mixture, after 4 and 8 hours, respectively, and heating was continued for additional 16 hours. After cooling to ambient temperature, the mixture was chromatographed on silicagel with dichloromethane as eluent. 0.145 g of the title compound was obtained as pale yellow solid.

Workup

temperatureafter 4 and 8 hours, respectively, and heating
temperatureAfter cooling to ambient temperature
customthe mixture was chromatographed on silicagel with dichloromethane as eluent

Sources & evidence

ORD record: ord-453fe73909c1401b937444069e113c8c
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115611B2

Reaction notes

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