Potassium Carbonate → HCID 90386861, compound

HRID 1424766Notes

Reaction equation

HRID 1424766 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Br:15].I[C:17]1[CH:18]=[C:19]([C:23]2[C:28]3[S:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[C:27]=3[CH:26]=[CH:25][CH:24]=2)[CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>[Cu].C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Br:15])[C:21]1[CH:22]=[CH:17][CH:18]=[C:19]([C:23]2[C:28]3[S:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[C:27]=3[CH:26]=[CH:25][CH:24]=2)[CH:20]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 4657530Bis(2-bromophenyl)amineHCID 90387091HCID 90387091, compound

Product 1

HCID 90386861HCID 90386861, compoundYield 46.9%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
200 °C

Procedure

Bis(2-bromophenyl)amine (7.15 g, 21.86 mmol), 4-(3-iodophenyl)dibenzo[b,d]thiophene (9.29 g, 24.05 mmol), copper (0.695 g, 10.93 mmol), and K2CO3 (6.04 g, 43.7 mmol) were added into a 50 mL flask. The neat solids were heated at 200° C. for 36 hours. The mixture was then cooled. DCM (250 mL) was added to solubilize the organic products. The solution was filtered through a pad of Celite® and washed several times with DCM. The crude material was purified via column chromatography using hexane/DCM (85/15). The product collected from the column was triturated with methanol and filtered to afford 2-bromo-N-(2-bromophenyl)-N-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)aniline (6.0 g, 10.25 mmol, 46.9% yield) as a yellowish powder.

Workup

  1. temperatureThe mixture was then cooled
  2. filtrationThe solution was filtered through a pad of Celite®
  3. washwashed several times with DCM
  4. customThe crude material was purified via column chromatography
  5. customThe product collected from the column
  6. customwas triturated with methanol
  7. filtrationfiltered

Sources & evidence

ORD record
ord-0009c3ed49004f12afcc48420369a51a
Source dataset
uspto-grants-2015_01
Patent number
US08927749B2

Reaction notes

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