Chloroform → HCID 54142217, compound

HRID 1938646Notes

Reaction equation

HRID 1938646 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][Cl:34])=[CH:25][CH:24]=2)=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(Cl)[Cl:36].ClN1C(=O)CCC1=O>C(OCC)(=O)C.CCCCCC>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH2:31][CH2:32][CH2:33][Cl:34])=[CH:27][CH:28]=2)=[C:16]([Cl:36])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 31398ChlorosuccinimideHCID 53730416HCID 53730416, compound

Product 1

HCID 54142217HCID 54142217, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Combine 1-(4-benzyloxyphenyl)-1-(4-(4-chlorobutyloxy)phenyl)-2-phenyl ethylene (3.5 g, 7.5 mmol) and chloroform 935 mL). Add N-chlorosuccinimide (1.99 g, 14.9 mmol). Heat at reflux. After 18 hours, cool the reaction mixture and extract with water, aqueous saturated sodium bicarbonate solution and water. Dry the organic layer over MgSO4, filter, and dry in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 10% ethyl acetate/hexane to give 1-(4-benzyloxyphenyl)-1-(4-(4-chlorobutyloxy)phenyl)-2-chloro-2-phenyl ethylene.

Workup

  1. temperatureHeat
  2. temperatureat reflux
  3. temperaturecool the reaction mixture
  4. extractionextract with water, aqueous saturated sodium bicarbonate solution and water
  5. dry with materialDry the organic layer over MgSO4
  6. filtrationfilter
  7. customdry in vacuo
  8. customto give a residue

Sources & evidence

ORD record
ord-4fcd9966bd284914883922628dafc3ad
Source dataset
uspto-grants-1997_12
Patent number
US05693674

Reaction notes

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