Boron tribromide → HCID 59660697, compound

HRID 1641431Notes

Reaction equation

HRID 1641431 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[N:8][N:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=2)[C:10]=1[CH3:11].B(Br)(Br)Br>C(Cl)Cl>[OH:18][C:15]1[CH:14]=[CH:13][C:12]([N:9]2[C:10]([CH3:11])=[C:6]([CH:2]=[O:1])[CH:7]=[N:8]2)=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 59660700HCID 59660700, compound

Product 1

HCID 59660697HCID 59660697, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 4-[1,3]dioxolan-2-yl-1-(4-methoxy-phenyl)-5-methyl-1H-pyrazole (0.2 g, 0.8 mmol) in CH2Cl2 (4 mL) was added boron tribromide (1M in DCM, 2.3 mL, 2.3 mmol) at −78° C. over 5 min. The reaction mixture was stirred at −78° C. for 1 h, and then at room temperature for 4 h. The reaction was quenched with sat. NaHCO3 at 0° C., extracted with CH2Cl2, washed brine, and dried over Na2SO4. After concentrated in vacuo, the title compound was obtained with a yield of 97% (150 mg), which was used to the next step without further purifications; MS (APCI) m/z: 203 (M+1, 100).

Workup

  1. waitat room temperature for 4 h
  2. customThe reaction was quenched with sat. NaHCO3 at 0° C.
  3. extractionextracted with CH2Cl2
  4. washwashed brine
  5. dry with materialdried over Na2SO4
  6. concentrationAfter concentrated in vacuo

Sources & evidence

ORD record
ord-55af63b4ce1e4c438692ef1a208d79a0
Source dataset
uspto-grants-2012_02
Patent number
US08115005B2

Reaction notes

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