Boron tribromide → HCID 23289170, compound

HRID 366343Notes

Reaction equation

HRID 366343 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8]C)[C:5]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[N:12]([CH3:21])[C:11]2=[O:22])=[C:4]([F:23])[CH:3]=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[C:5]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:18])([F:19])[F:20])[N:12]([CH3:21])[C:11]2=[O:22])=[C:4]([F:23])[CH:3]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 23289172HCID 23289172, compound

Product 1

HCID 23289170HCID 23289170, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.7 g (16 mmol) of 3-(4-chloro-2-fluoro-6-methoxyphenyl)-1-methyl-6-trifluoromethyluracil was dissolved in 100 ml of dichloromethane, and 27 ml (80 mmol) of boron tribromide (3.0M dichloromethane solution) was dropwise added 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 5.4 g (yield: 98.2%) of the desired product as white crystals. Melting point: 143-144° 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-5f7bad4827684a29a5d2b6ffcaf2b7b3
Source dataset
uspto-grants-2000_10
Patent number
US06130187

Reaction notes

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