Boron tribromide → 4-(1H-indazol-1-yl)phenol

HRID 598789Notes

Reaction equation

HRID 598789 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=[N:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>ClCCl>[N:9]1([C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[N:10]1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 11218363HCID 11218363, compound

Product 1

HCID 644360724-(1H-indazol-1-yl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

1-(4-Methoxyphenyl)-1H-indazole (30 mg, 0.134 mmol) was dissolved in dichloromethane (0.4 mL) and cooled to 40° C. Boron tribromide (0.4 mL, 1 M solution in dichloromethane, 0.4 mmol) was added, and the reaction was warmed to rt and stirred for 5 hours. Saturated sodium bicarbonate solution was added, and the mixture was extracted with dichloromethane. The extracts were dried over MgSO4 and concentrated to give the desired product. LC-MS (C13H10N2O calculated 210) m/z 211 (M+H).

Workup

  1. temperaturethe reaction was warmed to rt
  2. extractionthe mixture was extracted with dichloromethane
  3. dry with materialThe extracts were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-27ea307a23a9498cbf53f1f9bc6f5284
Source dataset
uspto-grants-2011_03
Patent number
US07897634B2

Reaction notes

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