Boron tribromide → HCID 67195220, compound

HRID 598766Notes

Reaction equation

HRID 598766 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:17]3[CH:16]4[CH2:18][CH2:19][CH2:20][CH2:21][CH: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>[CH3:22][C:11]1[C:12]2[CH2:13][CH2:14][CH:15]3[CH2:21][CH2:20][CH2:19][CH2:18][CH:16]3[C:17]=2[N:9]([C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=2)[N:10]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67197076HCID 67197076, compound

Product 1

HCID 67195220HCID 67195220, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

1-(4-Methoxyphenyl)-3-methyl-4,5,5a,6,7,8,9,9a-octahydro-1H-benzo[g]indazole (0.44 g, 1.49 mmol) was dissolved in dichloromethane (4 mL) and cooled to −40° C., and boron tribromide (0.5 mL) was added. The reaction was stirred for 2 hours, then carefully quenched with saturated sodium bicarbonate solution. The mixture was extracted with dichloromethane. The organic extracts were washed with brine, dried over MgSO4, and concentrated. The reaction was assumed to be quantitative. LC-MS (C18H22N2O calculated 282) m/z 283 (M+H).

Workup

  1. customcarefully quenched with saturated sodium bicarbonate solution
  2. extractionThe mixture was extracted with dichloromethane
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c8cc4cb4aa6e4081b98999919ab3cf2f
Source dataset
uspto-grants-2011_03
Patent number
US07897634B2

Reaction notes

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