Boron tribromide → HCID 135616893, compound

HRID 386404Notes

Reaction equation

HRID 386404 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([N:14]3[CH:20]4[CH2:21][CH2:22][N:17]([CH2:18][CH2:19]4)[CH2:16][CH2:15]3)=[N:11][N:10]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)(Cl)Cl>[N:17]12[CH2:18][CH2:19][CH:20]([CH2:21][CH2:22]1)[N:14]([C:12]1[O:13][C:9]([C:6]3[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=3)=[N:10][N:11]=1)[CH2:15][CH2:16]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 9972016HCID 9972016, compound

Product 1

HCID 135616893HCID 135616893, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-63 °C

Procedure

A mixture of 4-[5-(4-methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-1,4-diaza-bicyclo[3.2.2]nonane (1.0 g, 3.3 mmol) and chloroform (20 ml) was cooled to −63° C. A mixture of boron tribromide (5.4 g, 21.6 mmol) and chloroform (10 ml) was added at 60° C. The mixture was allowed to reach room-temperature. The crude mixture was purified by column chromatography on silica gel with dichloromethane, 10% methanol and 1% aqueous ammonia as solvent and gave the title compound. LC-ESI-HRMS of [M+H]+ shows 287.1514 Da. Calc. 287.150801 Da, dev. 2.1 ppm.

Workup

  1. additionwas added at 60° C
  2. customThe crude mixture was purified by column chromatography on silica gel with dichloromethane, 10% methanol and 1% aqueous ammonia as solvent

Sources & evidence

ORD record
ord-e1552c95018547188d53db4e4111f987
Source dataset
uspto-grants-2013_02
Patent number
US08372832B2

Reaction notes

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