Dichloromethane → HCID 89479855, compound

HRID 589245Notes

Reaction equation

HRID 589245 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:25]=[CH:24][C:8]([N:9]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1.[Br:26][C:27]1[CH:28]=[C:29]([C:40]2[CH:45]=[CH:44][C:43]([OH:46])=[CH:42][CH:41]=2)[S:30][C:31]=1[C:32]1[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(Cl)Cl>C(#N)C.CCO.O>[Br:26][C:27]1[CH:28]=[C:29]([C:40]2[CH:45]=[CH:44][C:43]([O:46][CH2:2][CH2:3][O:4][C:5]3[CH:25]=[CH:24][C:8]([N:9]([C:10]4[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=4)[C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=4)=[CH:7][CH:6]=3)=[CH:42][CH:41]=2)[S:30][C:31]=1[C:32]1[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 89479599HCID 89479599, compoundHCID 89479972HCID 89479972, compound

Product 1

HCID 89479855HCID 89479855, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

4-(2-bromoethoxy)-N,N-bis-(4-chlorophenyl)aniline (70, 1.40 g, 3.20 mmol) and 4-(4-bromo-5-(4-methoxyphenyl)thiophen-2-yl)phenol (65, 1.16 g, 3.20 mmol) were dissolved in acetonitrile (40 mL) and the cesium carbonate (2.09 g, 6.41 mmol) was added. The reaction mixture was heated to reflux for 20 hours. After cooling to RT, the reaction mixture was poured into DCM (100 mL) and water (150 mL). The mixture was mixed well and the aqueous portion extracted with DCM (2×100 mL). The combined organics were washed with water (2×150 mL), dried over MgSO4, filtered and solvent removed by rotary evaporation. The resulting off-white solid was sonicated in MeOH (100 mL), filtered and air dried to afford an off-white powder which still contained some minor impurities by TLC. This material was allowed to stir in refluxing EtOH (150 mL) for 15 minutes, cooled slightly, filtered and air dried to afford 71 as an off-white powder (1.60 g, 70%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 20 hours
  3. additionThe mixture was mixed well
  4. extractionthe aqueous portion extracted with DCM (2×100 mL)
  5. washThe combined organics were washed with water (2×150 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customsolvent removed by rotary evaporation
  9. customThe resulting off-white solid was sonicated in MeOH (100 mL)
  10. filtrationfiltered
  11. customair dried
  12. customto afford an off-white powder which
  13. temperaturecooled slightly
  14. filtrationfiltered
  15. customair dried

Sources & evidence

ORD record
ord-d1cf409ee9004a9ebcfd049b5ee42629
Source dataset
uspto-grants-2016_01
Patent number
US09227986B2

Reaction notes

Loading…