Boron tribromide → HCID 58256804, compound

HRID 598792Notes

Reaction equation

HRID 598792 reaction equation
[CH2:1]([C:3]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]([C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)[N:4]=1)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C:3]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]([C:10]2[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=2)[N:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58256810HCID 58256810, compound

Product 1

HCID 58256804HCID 58256804, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 3,5-diethyl-1-(4-methoxyphenyl)-1H-pyrazole (893 mg, 3.88 mmol) in methylene chloride (50 mL) at −78° C. was added boron tribromide (1.10 mL, 11.63 mmol). The reaction was stirred at −78° C. for 1 hour and at room temperature for an additional 1 hour. The reaction was quenched with saturated sodium bicarbonate. After the aqueous layer was extracted with methylene chloride, the combined organic layers were dried (MgSO4) and concentrated to give the desired product. The reaction was assumed to be quantitative. LC-MS (C13H16N2O calculated 216) m/z 217 (M+H).

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate
  2. extractionAfter the aqueous layer was extracted with methylene chloride
  3. dry with materialthe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b8b8a968021c4a30998d74fe7162e753
Source dataset
uspto-grants-2011_03
Patent number
US07897634B2

Reaction notes

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