Dimethyl Sulfoxide → HCID 15661440, compound

HRID 1087022Notes

Reaction equation

HRID 1087022 reaction equation
ClCCl.C(Cl)(=O)C(Cl)=O.CS(C)=O.[Br:14][C:15]1[CH:16]=[C:17]([CH2:29][O:30][C:31](=[O:33])[CH3:32])[C:18]2[CH:19]([OH:28])[C:20]3[C:25]([C:26]=2[CH:27]=1)=[CH:24][CH:23]=[CH:22][CH:21]=3>CCN(CC)CC>[Br:14][C:15]1[CH:16]=[C:17]([CH2:29][O:30][C:31](=[O:33])[CH3:32])[C:18]2[C:19](=[O:28])[C:20]3[C:25]([C:26]=2[CH:27]=1)=[CH:24][CH:23]=[CH:22][CH:21]=3

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344Dichloromethane2×HCID 65578Oxalyl chlorideHCID 15661438HCID 15661438, compound

Product 1

HCID 15661440HCID 15661440, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Dichloromethane (5 ml) was cooled to -60° under N2, oxalyl chloride (1.65 ml, 1M solution in CH2Cl2, 1.1 eq) was added followed by DMSO (234 ml in 1 ml of CH2Cl2). The resulting solution was stirred at -60° for 10 min. 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. Et3N (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 extract was dried without further purification in the next step. ##STR406##

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 extract
  10. customwas dried without further purification in the next step

Sources & evidence

ORD record
ord-3d72481d5230489792f7f1e108c1ccdb
Source dataset
uspto-grants-1991_07
Patent number
US05034384

Reaction notes

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