Boron tribromide → HCID 23289194, compound

HRID 366346Notes

Reaction equation

HRID 366346 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([O:9]C)[C:3]=1[N:11]1[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]1=[O:23].B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([OH:9])[C:3]=1[N:11]1[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[N:13]([CH3:22])[C:12]1=[O:23]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 23289195HCID 23289195, compound

Product 1

HCID 23289194HCID 23289194, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

13.6 g (40 mmol) of 3-(2,4-difluoro-6-methoxyphenyl)-1-methyl-6-trifluoromethyluracil was dissolved in 150 ml of dichloromethane, and 66.7 ml (200 mmol) of boron tribromide (3.0M dichloromethane solution) was dropwise added thereto at 0° 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 9.8 g (yield: 75.4%) of the desired product as white crystals. Melting point: 195-196° C.

Workup

  1. customat 0° C
  2. extractionIt was extracted with dichloromethane
  3. washThe organic layer was washed sequentially with water
  4. dry with materiala saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThen, the obtained crude crystals
  7. washwere washed with isopropyl ether

Sources & evidence

ORD record
ord-4eee9085c4e04b5b8085d622ad0b8e77
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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