Boron tribromide → HCID 58256804, compound
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
Product 1
Reagents, catalysts & solvents 1
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
- customThe reaction was quenched with saturated sodium bicarbonate
- extractionAfter the aqueous layer was extracted with methylene chloride
- dry with materialthe combined organic layers were dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-998c56ddb0a348c0bb7c3a8852a5cf8a
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07981896B2
Reaction notes
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