Boron tribromide → 1-(4-Fluorophenyl)-1H-indazol-5-ol

HRID 13170Notes

Reaction equation

HRID 13170 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17]C)=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 593396221-(4-Fluorophenyl)-5-methoxy-1H-indazole

Product 1

HCID 593397691-(4-Fluorophenyl)-1H-indazol-5-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-Fluorophenyl)-5-methoxy-1H-indazole (137e, 1.0 mmol, 242 mg) was dissolved in dichloromethane (4 ml) and BBr3 (4 ml, 1 M in dichloromethane) was added. The reaction mixture was stirred in r.t. overnight before it was quenched with water (20 ml). The product was extracted with dichloromethane (2×20 ml) and washed with sat. NaHCO3. The organic phase was dried over Na2SO4, concentrated and purified by flash chromatography on silica gel (heptane-ethyl acetate).

Workup

  1. customwas quenched with water (20 ml)
  2. extractionThe product was extracted with dichloromethane (2×20 ml)
  3. washwashed with sat. NaHCO3
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography on silica gel (heptane-ethyl acetate)

Sources & evidence

ORD record
ord-9c8037f6808c460f81a2bff0bb6d58d7
Source dataset
uspto-grants-2010_06
Patent number
US07728030B2

Reaction notes

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