Boron tribromide → HCID 136340575, compound
Reaction equation
C([O:7][C:8]1[CH:13]=[C:12]([C:14]2[O:18][C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]4[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=4)[CH:20]=3)=[N:16][N:15]=2)[C:11]([O:35]CCCCCC)=[CH:10][C:9]=1[C:42]1[O:46][C:45]([C:47]2[CH:52]=[CH:51][CH:50]=[C:49]([O:53][C:54]3[CH:59]=[CH:58][C:57]([N+:60]([O-:62])=[O:61])=[CH:56][CH:55]=3)[CH:48]=2)=[N:44][N:43]=1)CCCCC.B(Br)(Br)Br>ClCCl>[N+:60]([C:57]1[CH:56]=[CH:55][C:54]([O:53][C:49]2[CH:48]=[C:47]([C:45]3[O:46][C:42]([C:9]4[CH:10]=[C:11]([OH:35])[C:12]([C:14]5[O:18][C:17]([C:19]6[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]7[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=7)[CH:20]=6)=[N:16][N:15]=5)=[CH:13][C:8]=4[OH:7])=[N:43][N:44]=3)[CH:52]=[CH:51][CH:50]=2)=[CH:59][CH:58]=1)([O-:62])=[O:61]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3.04 g of 5,5′-(2,5-bis(hexyloxy)-1,4-phenylene)bis(2-(3-(4-nitrophenoxy)phenyl)-1,3,4-oxadiazole) (3.6 mmol) prepared in Synthesis Example 9 was dissolved in 120 ml of dichloromethane at −78□, and 3.5 ml of boron tribromide (35.6 mmol) was added thereto, followed by slowly raising the temperature to 0□. Thereafter, the reaction was quenched by addition of methanol, followed by adding excess water. The resultant solution was neutralized with dichloromethane, filtered, and performing silica gel column chromatography (developed with trichloromethane) to yield 0.4 g of a product having Formula 38. 1H NMR (300 MHz, CDCl3) analytical results of the product were as follows:
Workup
- additionwas added
- temperatureby slowly raising the temperature to 0□
- customThereafter, the reaction was quenched by addition of methanol
- additionby adding excess water
- filtrationfiltered
Sources & evidence
- ORD record
- ord-65f2afd4d3ed46829c4443b98e1688fe
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09106057B2
Reaction notes
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