Norbornadiene → HCID 59749439, compound

HRID 747185Notes

Reaction equation

HRID 747185 reaction equation
[N:1]([CH2:4][CH:5]1[O:9][N:8]=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)[CH2:6]1)=[N+:2]=[N-:3].[CH:17]12CC(C=C1)C=[CH:18]2>O1CCOCC1>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]2[CH2:6][CH:5]([CH2:4][N:1]3[CH:18]=[CH:17][N:3]=[N:2]3)[O:9][N:8]=2)=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 8473NorbornadieneHCID 179544685-Azidomethyl-3-(4-bromo-phenyl)-4,5-dihydro-isoxazole

Product 1

HCID 59749439HCID 59749439, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

5-Azidomethyl-3-(4-bromo-phenyl)-4,5-dihydro-isoxazol (12.3 g, 43.6 mmol) and bicyclo[2.2.1]hepta-2,5-diene (23.6 ml, 218.1 mmol) were added to dioxane (200 ml), heated to 100° C. and stirred for six hours. The reaction mixture was concentrated in vacuo followed by addition of ethyl ether (200 ml). The precipitate was collected and washed with ethyl ether (3×20 ml) and dried under nitrogen to give the desired product (8.8 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionfollowed by addition of ethyl ether (200 ml)
  3. customThe precipitate was collected
  4. washwashed with ethyl ether (3×20 ml)
  5. customdried under nitrogen

Sources & evidence

ORD record
ord-3e50b0ba231a47a58d07fc81d02524df
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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