Boron tribromide → HCID 58330951, compound

HRID 241493Notes

Reaction equation

HRID 241493 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[C:4]([N:14]([C:28]2[CH:33]=[CH:32][C:31]([O:34]C)=[CH:30][CH:29]=2)[C:15]2[C:20]3[S:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:19]=3[CH:18]=[CH:17][CH:16]=2)=[CH:3][CH:2]=1.B(Br)(Br)Br>ClCCl>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[C:4]([N:14]([C:15]2[C:20]3[S:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:19]=3[CH:18]=[CH:17][CH:16]=2)[C:28]2[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58330962HCID 58330962, compound

Product 1

HCID 58330951HCID 58330951, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(dibenzo[b,d]thiophen-4-yl)-N-(4-methoxyphenyl)dibenzo[b,d]thiophen-4-amine (4.6 g, 9.4 mmol) was dissolved in 100 mL of anhydrous dichloromethane. The solution was cooled with a dry ice/isopropanol bath. To the solution was added boron tribromide solution in hexanes (1.0 M solution, 16 mL). The reaction was allowed to warm to room temperature for 6 h. The reaction was quenched with water. The product was purified with column chromatography using dichloromethane as eluent. 4 g of desired product was obtained. (90% yield)

Workup

  1. temperatureThe solution was cooled with a dry ice/isopropanol bath
  2. customThe reaction was quenched with water
  3. customThe product was purified with column chromatography

Sources & evidence

ORD record
ord-0a1dc34634044ae2bdf6a93108812d93
Source dataset
uspto-grants-2014_02
Patent number
US08652653B2

Reaction notes

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