Boron tribromide → HCID 67195220, compound

HRID 1013024Notes

Reaction equation

HRID 1013024 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-b448d4d1bfa443b38b298f88add3a5f8
Source dataset
uspto-grants-2011_07
Patent number
US07981896B2

Reaction notes

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