Boron tribromide → 4-(7-phenyl-2-propyl-2H-indazol-3-yl)phenol

HRID 1295044Notes

Reaction equation

HRID 1295044 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]([CH2:24][CH2:25][CH3:26])[N:11]=[C:12]3[C:17]=2[CH:16]=[CH:15][CH:14]=[C:13]3[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[C:18]1([C:13]2[C:12]3[C:17](=[C:9]([C:6]4[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=4)[N:10]([CH2:24][CH2:25][CH3:26])[N:11]=3)[CH:16]=[CH:15][CH:14]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 688851453-(4-methoxyphenyl)-7-phenyl-2-propyl-2H-indazole

Product 1

HCID 1363584774-(7-phenyl-2-propyl-2H-indazol-3-yl)phenolYield 34.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-methoxyphenyl)-7-phenyl-2-propyl-2H-indazole (0.140 g, 0.43 mmol) in CH2Cl2 (5 mL) was added BBr3 (0.081 mL, 0.865 mmol) at −78° C. The solution was stirred for 15 minutes and allowed to stand overnight in the refrigerator. The reaction was quenched with NH4OH (10 mL) and extracted with CH2Cl2. The organic layer was washed with water and dried (MgSO4). The reaction was purified by flash chromatography (5/1 hexane/ethyl Acetate) to give the title compound as a white solid (0.066 g, 0.15 mmol, 34%).

Workup

  1. waitto stand overnight in the refrigerator
  2. customThe reaction was quenched with NH4OH (10 mL)
  3. extractionextracted with CH2Cl2
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. customThe reaction was purified by flash chromatography (5/1 hexane/ethyl Acetate)

Sources & evidence

ORD record
ord-2dd37ce6accc4951bb93b1ada2e0c057
Source dataset
uspto-grants-2007_07
Patent number
US07241791B2

Reaction notes

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