Boron tribromide → HCID 68156573, compound

HRID 1892676Notes

Reaction equation

HRID 1892676 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)=[C:5]([CH3:18])[CH:4]=1.B(Br)(Br)Br>ClCCl.CO.O>[N:10]1[N:9]([C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][C:5]=2[CH3:18])[CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[CH:15]2

Participants

6

Reactant 2

HCID 25134Boron tribromideHCID 68157489HCID 68157489, compound

Product 1

HCID 68156573HCID 68156573, compoundYield 74.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of 2-(4-methoxy-2-methylphenyl)-2H-indazole (500 mg, 2.1 mmol) in dichloromethane (10 mL) was cooled to −78° C. Added boron tribromide (2.6 g, 10.5 mmol) and reaction was stirred at −78° C. for 1 hour. Reaction was warmed to room temperature are stirred overnight. The reaction was diluted with methanol and water, and extracted with ethyl acetate (3×30 mL). The combined organics were washed with water and brine, dried over sodium sulfate, filtered, and concentrated to give 4-(2H-indazol-2-yl)-3-methylphenol (350 mg, 74%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6, δ): 9.82 (s, 1H), 8.51 (s, 1H), 7.76 (d, J=8.4 Hz, 1H), 7.68 (d, J=8.8 Hz, 1H), 7.25-7.30 (m, 2H), 7.07-7.11 (m, 1H), 6.80 (d, J=2.4 Hz, 1H), 6.75 (dd, J=8.4, 2.4 Hz, 1H), 2.06 (s, 3H).

Workup

  1. customReaction
  2. temperaturewas warmed to room temperature
  3. stirringare stirred overnight
  4. extractionextracted with ethyl acetate (3×30 mL)
  5. washThe combined organics were washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6bbb355c0db2476aa2178be69b0bad34
Source dataset
uspto-grants-2013_08
Patent number
US08507533B2

Reaction notes

Loading…