Boron Trichloride → HCID 22349441, compound

HRID 896033Notes

Reaction equation

HRID 896033 reaction equation
C[O:2][C:3]1[CH:26]=[CH:25][C:6]([O:7][C:8]2[CH:16]=[CH:15][C:14]3[C:10](=[CH:11][N:12]([C:17]4[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=4)[N:13]=3)[CH:9]=2)=[CH:5][CH:4]=1.B(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:2][C:3]1[CH:26]=[CH:25][C:6]([O:7][C:8]2[CH:16]=[CH:15][C:14]3[C:10](=[CH:11][N:12]([C:17]4[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=4)[N:13]=3)[CH:9]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 25135Boron TrichlorideHCID 516892Sodium BicarbonateHCID 22349424HCID 22349424, compound

Product 1

HCID 22349441HCID 22349441, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of 4-[5-(4-Methoxy-phenoxy)-indazol-2-yl]-benzonitrile (0.075 grams, 0.22 mmol) in 1.6 mL of methylene chloride was treated with tetrabutylammonium iodide (0.13 grams, 0.36 mmol). After cooling to −78° C., the mixture was treated dropwise with a solution of BCl3 in methylene chloride (0.81 mL, 1 M, 0.81 mmol). After stirring for 20 minutes, the mixture was slowly warmed to room temperature and was stirred for 1 hour. The mixture was cautiously neutralized with saturated aqueous sodium bicarbonate, and the aqueous layer was extracted 3 times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo, affording 0.070 grams of 4-[5-(4-Hydroxy-phenoxy)-indazol-2-yl]-benzonitrile as a colorless solid. MS: 328.4 [M+H]+; 326.4 [M−H]−

Workup

  1. temperaturethe mixture was slowly warmed to room temperature
  2. stirringwas stirred for 1 hour
  3. extractionthe aqueous layer was extracted 3 times with ethyl acetate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92dcdb364283492ea48f9a1810ea3130
Source dataset
uspto-grants-2005_07
Patent number
US06919332B2

Reaction notes

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