Boron tribromide → HCID 58948773, compound

HRID 1013017Notes

Reaction equation

HRID 1013017 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[C:16]4[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=4[CH2:14][CH2:13][C:12]=3[C:11]([CH3:22])=[N:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl.C([O-])(O)=O.[Na+]>[CH3:22][C:11]1[C:12]2[CH2:13][CH2:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[C:17]=2[N:9]([C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=2)[N:10]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 58948768HCID 58948768, compound

Product 1

HCID 58948773HCID 58948773, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
-40 °C

Procedure

1-(4-Methoxyphenyl)-3-methyl-4,5-dihydro-1H-benzo[g]indazole (200 mg, 0.69 mmol) was dissolved in dichloromethane (2 mL) under N2 and cooled to −40° C. Boron tribromide (2.07 mL, 1 M in dichloromethane, 2.07 mmol) was added dropwise and the solution was stirred for 4 hours, warming to room temperature. The reaction mixture was carefully diluted with saturated NaHCO3 solution. The mixture was extracted with dichloromethane, and the extracts were dried over MgSO4 and concentrated. SiO2 chromatography with 20-80% ethyl acetate/hexanes gave 144 mg of the desired product (76% yield). LC-MS (C18H16N2O calculated 276) m/z 277 (M+H).

Workup

  1. temperaturewarming to room temperature
  2. extractionThe mixture was extracted with dichloromethane
  3. dry with materialthe extracts were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d8908f59be184587b144d4c3fcfdc98f
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

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