Boron tribromide → HCID 23368377, compound

HRID 1901630Notes

Reaction equation

HRID 1901630 reaction equation
[NH2:1][CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[CH:16]=1)[CH2:3][O:4][C:5]1[C:9]2[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=2[O:7][N:6]=1.B(Br)(Br)Br>C(Cl)Cl>[NH2:1][CH:2]([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=1)[CH2:3][O:4][C:5]1[C:9]2[CH:10]=[C:11]([Cl:14])[CH:12]=[CH:13][C:8]=2[O:7][N:6]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 23368481HCID 23368481, compound

Product 1

HCID 23368377HCID 23368377, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2.3 g of 3-[2-amino-2-(3-methoxyphenyl)ethoxy]-5-chloro-1,2-benzoisoxazole in 20 ml of methylene chloride is dropwise added 22 ml of a methylene chloride solution (1.0M) of boron tribromide over 15 minutes with ice-cooling, and they are subjected to reaction at the same temperature for 30 minutes. Subsequently, insolubles are removed by filtration, and water and ethyl acetate are added to the filtrate. The pH is adjusted to 8.5 with a 10% aqueous sodium hydroxide solution, and after shaking, the crystals precipitated are collected by filtration. The organic layer of the filtrate is separated, and the organic layer is washed with a saturated saline solution and dried over anhydrous magnesium sulfate, after which the solvent is removed by distillation under reduced pressure. The crystals obtained are combined with the crystals previously obtained by filtration and dried, to obtain 2.0 g of colorless, crystalline 3-[2-amino-2-(3-hydroxyphenyl)ethoxy]-5-chloro-1,2-benzoisoxazole.

Workup

  1. customover 15 minutes
  2. temperaturecooling
  3. customthey are subjected to reaction at the same temperature for 30 minutes
  4. customSubsequently, insolubles are removed by filtration, and water and ethyl acetate
  5. additionare added to the filtrate
  6. customthe crystals precipitated
  7. filtrationare collected by filtration
  8. customThe organic layer of the filtrate is separated
  9. washthe organic layer is washed with a saturated saline solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customafter which the solvent is removed by distillation under reduced pressure
  12. customThe crystals obtained
  13. custompreviously obtained by filtration
  14. customdried

Sources & evidence

ORD record
ord-27900d5d1fa14af38c36be68af5f6433
Source dataset
uspto-grants-1996_11
Patent number
US05578627

Reaction notes

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