Dimethyl Sulfoxide → HCID 15661440, compound

HRID 1493845Notes

Reaction equation

HRID 1493845 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Br:11][C:12]1[CH:13]=[C:14]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[C:15]2[CH:16]([OH:25])[C:17]3[C:22]([C:23]=2[CH:24]=1)=[CH:21][CH:20]=[CH:19][CH:18]=3.C(N(CC)CC)C>C(Cl)Cl>[Br:11][C:12]1[CH:13]=[C:14]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[C:15]2[C:16](=[O:25])[C:17]3[C:22]([C:23]=2[CH:24]=1)=[CH:21][CH:20]=[CH:19][CH:18]=3

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 15661438HCID 15661438, compound

Product 1

HCID 15661440HCID 15661440, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

Dichloromethane (5 ml) was cooled to -60° C. under N2, oxalyl chloride (1.65 ml, 1M soln in CH2Cl2, 1.1 eq) was added followed by DMSO (234 μl in 1 ml of (CH2Cl2). The resulting solution was stirred at -60° for 10 minutes. The 3-bromo-1-acetoxymethyl-9-fluorenol (0.480 g) in a suspension of CH2Cl2 (2 ml) was added dropwise and the solution stirred at -60° for 0.5 hour. Triethylamine (1.06 ml) was added dropwise and the solution stirred at -60° for 15 minutes. The cooling bath was removed and water (5 ml) was added and the reaction mixture stirred at room temperature for 20 minutes. The organic phase was separated and the aqueous phase was extracted with EtOAc, the combined organic extract was dried and evaporated which gave product, one spot on tlc, used without further purification in the next step. ##STR37##

Workup

  1. additionwas added dropwise
  2. stirringthe solution stirred at -60° for 0.5 hour
  3. stirringthe solution stirred at -60° for 15 minutes
  4. customThe cooling bath was removed
  5. additionwater (5 ml) was added
  6. stirringthe reaction mixture stirred at room temperature for 20 minutes
  7. customThe organic phase was separated
  8. extractionthe aqueous phase was extracted with EtOAc
  9. extractionthe combined organic extract
  10. customwas dried
  11. customevaporated which
  12. customgave product, one spot on tlc
  13. customused without further purification in the next step

Sources & evidence

ORD record
ord-c0f685ffe0fe4def9782ec30da172e15
Source dataset
uspto-grants-1991_06
Patent number
US05025007

Reaction notes

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