Water → HCID 19709698, compound

HRID 725807Notes

Reaction equation

HRID 725807 reaction equation
N[C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[C:11]([C:16]([F:19])([F:18])[F:17])[CH:10]=2)[CH:5]=[C:4]([O:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=2)[N:3]=1.C(ON=O)(C)(C)C.O.C(Cl)(Cl)(Cl)[Cl:41]>>[F:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:4]2[CH:5]=[C:6]([O:8][C:9]3[CH:14]=[CH:13][C:12]([F:15])=[C:11]([C:16]([F:19])([F:18])[F:17])[CH:10]=3)[N:7]=[C:2]([Cl:41])[N:3]=2)=[CH:22][C:23]=1[C:28]([F:31])([F:30])[F:29]

Participants

5

Reactant 4

HCID 962WaterHCID 5943Carbon TetrachlorideHCID 10906Tert-Butyl nitriteHCID 19709693HCID 19709693, compound

Product 1

HCID 19709698HCID 19709698, compound

Conditions

Temperature
30 °C

Procedure

2-Amino-4,6-bis(4-fluoro-3-trifluoromethylphenoxy)pyrimidine (3.0 g, 6.7 mmol) was dissolved in carbon tetrachloride (75 ml) and the resulting solution was treated with t-butylnitrite (1.2 ml, 13.4 mmol). The mixture was heated at 30° C. for 48 hours and then poured into water. The product was extracted in dichloromethane, dried over sodium sulphate, filtered and concentrated under reduced pressure. The product, 4,6-bis(4-fluoro-3-trifluoromethyl-phenoxy)-2-chloro-pyrimidine, was obtained as an oil by column chromatography (eluting with 5:1, hexane:ethyl acetate). Yield 0.3 g (10%); mass 471 (M+ +H); N.m.r: 7.3-7.5 (6H, m, aromatics), 6.35 (1H,s,H-5).

Workup

  1. extractionThe product was extracted in dichloromethane
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-866f09efb98d430baf6efd1873a0e11a
Source dataset
uspto-grants-1998_01
Patent number
US05707995

Reaction notes

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