Water → 3-(3-Bromo-4-chloro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil

HRID 366337Notes

Reaction equation

HRID 366337 reaction equation
[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH3:11])[O:10][C:6]=2[C:5]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]2=[O:24])=[CH:4][CH:3]=1.[Br:25]Br.O>C(O)(=O)C>[Br:25][C:8]1[C:7]2[C:2]([Cl:1])=[CH:3][CH:4]=[C:5]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[C:6]=2[O:10][C:9]=1[CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 232891903-(4-Chloro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil

Product 1

HCID 232891933-(3-Bromo-4-chloro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracilYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.0 g (2.8 mmol) of 3-(4-chloro-2-methylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil was dissolved in 30 ml of acetic acid, and 0.9 g (5.6 mmol) of bromine was dropwise added thereto at room temperature. After completion of the dropwise addition, stirring was carried out at 40° C. for 6 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and 10% aqueous ammonia and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.6 g (yield: 50.0%) of a pale yellow glassy substance. Refractive index: 1.5632 (20° C.).

Workup

  1. customat room temperature
  2. additionAfter completion of the dropwise addition
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed sequentially with water and 10% aqueous ammonia
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThen, the obtained residue was purified by silica gel column chromatography
  9. customto obtain 0.6 g (yield: 50.0%) of a pale yellow glassy substance
  10. customRefractive index: 1.5632 (20° C.)

Sources & evidence

ORD record
ord-b0f9de72a779419e93b7bb6b702f494b
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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