Boron tribromide → 4-Indazol-2-ylphenol

HRID 598784Notes

Reaction equation

HRID 598784 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:17]=[C:16]3[C:11]([CH:12]=[CH:13][CH:14]=[CH:15]3)=[N:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[N:10]1[N:9]([C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)[CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[CH:15]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 12147772-(4-methoxyphenyl)-2H-indazole

Product 1

HCID 114243544-Indazol-2-ylphenolYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-(4-methoxyphenyl)-2H-indazole (50 mg, 0.22 mmol) in methylene chloride (3 mL) at −78° C. was added boron tribromide (62 μL, 0.66 mmol). The reaction was stirred at −78° C. for 1 hour and room temperature for 1 hour. The reaction was quenched with saturated sodium bicarbonate solution. After the aqueous layer was extracted with methylene chloride, the combined organic layers were dried (MgSO4) and concentrated to give 28.4 mg of the desired indazole. LC-MS (C13H10N2O calculated 210) m/z 211 (M+H).

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate solution
  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-a1492276d8964ff18ce230f3ca53b969
Source dataset
uspto-grants-2011_03
Patent number
US07897634B2

Reaction notes

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