Water → HCID 89479972, compound

HRID 589244Notes

Reaction equation

HRID 589244 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[CH:10][CH:9]=1.[Br:29][CH2:30][CH2:31]Br.O>C(#N)C>[Br:29][CH2:30][CH2:31][O:21][C:18]1[CH:19]=[CH:20][C:15]([N:14]([C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=2)[C:11]2[CH:12]=[CH:13][C:8]([Cl:7])=[CH:9][CH:10]=2)=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 10796Cesium carbonateHCID 89479694HCID 89479694, compound

Product 1

HCID 89479972HCID 89479972, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a 250 mL rbf was added cesium carbonate (4.93 g, 15.14 mmol) and anhydrous acetonitrile (50 mL). A solution of 4-(bis(4-chlorophenyl)amino)phenol (69, 2.5 g, 7.57 mmol) in acetonitrile (25 mL) was added, and an immediate light purple colour was observed. 1,2-dibromoethane (7.11 g, 37.9 mmol) was added and the reaction was heated to reflux for 5 days. After cooling to RT, the reaction mixture was poured into water (250 mL), mixed well and separated. The aqueous portion was extracted with EtOAc (2×100 mL) and the combined organics were washed with water (2×250 mL), dried over MgSO4, filtered and solvent removed by rotary evaporation. Flash chromatography (2% EtOAc/hexanes) afforded 70 as a clear, colourless oil (1.42 g, 43%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 5 days
  3. additionmixed well
  4. customseparated
  5. extractionThe aqueous portion was extracted with EtOAc (2×100 mL)
  6. washthe combined organics were washed with water (2×250 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customsolvent removed by rotary evaporation

Sources & evidence

ORD record
ord-bddfb721b937440593a1a0dd36db44f9
Source dataset
uspto-grants-2016_01
Patent number
US09227986B2

Reaction notes

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