Boron tribromide → HCID 67011542, compound

HRID 467432Notes

Reaction equation

HRID 467432 reaction equation
[C:1]1([CH3:56])[CH:6]=[CH:5][C:4]([N:7]([C:49]2[CH:54]=[CH:53][C:52]([CH3:55])=[CH:51][CH:50]=2)[C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:48]=[CH:47][C:17]([N:18]([C:33]4[CH:38]=[CH:37][C:36]([C:39]5[CH:44]=[CH:43][C:42]([O:45]C)=[CH:41][CH:40]=5)=[CH:35][CH:34]=4)[C:19]4[CH:24]=[CH:23][C:22]([C:25]5[CH:30]=[CH:29][C:28]([O:31]C)=[CH:27][CH:26]=5)=[CH:21][CH:20]=4)=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.B(Br)(Br)Br>C(Cl)Cl>[C:52]1([CH3:55])[CH:51]=[CH:50][C:49]([N:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:56])=[CH:2][CH:3]=2)[C:8]2[CH:9]=[CH:10][C:11]([C:14]3[CH:15]=[CH:16][C:17]([N:18]([C:19]4[CH:24]=[CH:23][C:22]([C:25]5[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=5)=[CH:21][CH:20]=4)[C:33]4[CH:34]=[CH:35][C:36]([C:39]5[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=5)=[CH:37][CH:38]=4)=[CH:47][CH:48]=3)=[CH:12][CH:13]=2)=[CH:54][CH:53]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67010213HCID 67010213, compound

Product 1

HCID 67011542HCID 67011542, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In a reaction vessel equipped with an agitator, thermometer and a cooling pipe, 2.73 g of N,N-di-p-tolyl-N′,N′-bis(4′-methoxybiphenyl-4-yl)benzidine and 100 mL of methylene chloride were placed. While the vessel was being cooled with ice, 10 mL of a 1M methylene chloride solution of boron tribromide was delivered by drops into the vessel, and furthermore the mixture was reacted at the same temperature for three hours. Then, the reacted solution was poured into ice water and extracted with methylene chloride. The organic layer was washed with water and separated, and it was then dried with magnesium sulfate and subjected to vacuum concentration. The residue was purified with a silica gel chromatography with a mixture of n-hexane and ethyl acetate as a solvent, where the ratio of n-hexane to ethyl acetate in the mixture was one to one. Thus, the objective product was obtained with the yield of 2.53 g.

Workup

  1. customIn a reaction vessel equipped with an agitator
  2. customwas reacted at the same temperature for three hours
  3. extractionextracted with methylene chloride
  4. washThe organic layer was washed with water
  5. customseparated
  6. dry with materialit was then dried with magnesium sulfate
  7. concentrationsubjected to vacuum concentration
  8. customThe residue was purified with a silica gel chromatography with a mixture of n-hexane and ethyl acetate as a solvent
  9. customThus, the objective product was obtained with the yield of 2.53 g

Sources & evidence

ORD record
ord-078f27d0440e402b8e6be443f3577b00
Source dataset
uspto-grants-2014_01
Patent number
US08623577B2

Reaction notes

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