Boron tribromide → 5-Amino-1-(4-fluorophenyl)4-[3-hydroxybenzoyl]pyrazole

HRID 429366Notes

Reaction equation

HRID 429366 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[CH:16]=1.B(Br)(Br)Br>C(Cl)Cl.[Cl-].[Na+].O>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=2)[N:5]=[CH:4][C:3]=1[C:14](=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 116020395-Amino-1-(4-fluorophenyl)-4-(3-methoxybenzoyl)pyrazole

Product 1

HCID 115439135-Amino-1-(4-fluorophenyl)4-[3-hydroxybenzoyl]pyrazoleYield 80.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To an ice-cooled solution of 5-amino-1-(4-fluorophenyl)-4-(3-methoxybenzoyl)pyrazole (3.0 g, 10.0 mmol) in methylene chloride (25 ml) was added boron tribromide (51 ml, 51 mmol, 1 M solution in methylene chloride). After 1 h, the reaction mixture was poured into brine and the product was extracted into ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give 5-amino-1-(4-fluorophenyl)-4-[3-hydroxybenzoyl]pyrazole (2.4 g).

Workup

  1. extractionthe product was extracted into ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4789ccb547704228bdf0789e48bf07f8
Source dataset
uspto-grants-2001_11
Patent number
US06316466B1

Reaction notes

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