Boron tribromide → 4-Chloro-2-hydroxyphenyl-1-methyl-6-trifluoromethyluracil

HRID 366344Notes

Reaction equation

HRID 366344 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]([CH3:19])[C:9]2=[O:20])=[C:4]([O:21]C)[CH:3]=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:16])[F:17])[N:10]([CH3:19])[C:9]2=[O:20])=[C:4]([OH:21])[CH:3]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 232891923-(4-Chloro-2-methoxyphenyl)-1-methyl-6-trifluoromethyluracil

Product 1

HCID 232891734-Chloro-2-hydroxyphenyl-1-methyl-6-trifluoromethyluracilYield 70.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

41.0 g (122.5 mmol) of 3-(4-chloro-2-methoxyphenyl)-1-methyl-6-trifluoromethyluracil was dissolved in 1000 ml of dichloromethane, and 470 ml (470.8 mmol) of boron tribromide (1.0M dichloromethane solution) was dropwise added at from -10° C. to -5° C. After stirring at room temperature for 3 hours, the reaction solution was poured into ice water and neutralized with sodium hydrogencarbonate. It was extracted with dichloromethane. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained crude crystals were washed with isopropyl ether to obtain 27.6 g (yield: 70.3%) of the desired product as white crystals. Melting point: 198-202° C.

Workup

  1. extractionIt was extracted with dichloromethane
  2. washThe organic layer was washed sequentially with water
  3. dry with materiala saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customThen, the obtained crude crystals
  6. washwere washed with isopropyl ether

Sources & evidence

ORD record
ord-cbdab467ea984eeb85ceb942bea05958
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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