Methanesulfonic Acid → HCID 22475896, compound

HRID 1383709Notes

Reaction equation

HRID 1383709 reaction equation
[Br:1][C:2]1[C:3](=O)[C:4]2[C:12](=[CH:13][CH:14]=1)[C:11]1[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=1)[CH:5]=2.[C:17]1([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CS(O)(=O)=O.S[CH2:36][CH2:37][C:38]([OH:40])=O>CO>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[C:5]([C:2]3[CH:3]=[CH:4][C:12]([O:40][C:38]4[CH:37]=[CH:36][CH:7]=[CH:6][CH:5]=4)=[CH:13][CH:14]=3)([C:27]3[CH:26]=[CH:25][C:24]([O:23][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:29][CH:28]=3)[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 6395Methanesulfonic AcidHCID 65143-Mercaptopropionic AcidHCID 7583Diphenyl EtherHCID 534201032,7Dibromofluorenone

Product 1

HCID 22475896HCID 22475896, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred mixture of 2,7-dibromofluorenone (26 g, 77 mmoles) and phenyl ether (170 g, 1 mole) is added 60 mL of methanesulfonic acid and 0.5 mL of 3-mercaptopropionic acid. The mixture is heated and stirred at 60° C. for 30 minutes, and then at 25° C. for 16 hours. The mixture is again stirred at 60° C. for 30 minutes and then at 25° C. for 3 hours. The mixture is poured into 1.4 L of ice water and 200 mL of methanol and allowed to stand in the hood for 4 days. The semi-solid precipitate is separated by decanting the supernatant liquid and then digesting with 1:1 v/v acetonitrile-hexane. The title compound is obtained as a colorless powder (32 g, 64 percent), melting point 178° C. to 180° C. HPLC analysis shows a purity of greater than 99 percent and the PMR spectrum (DMSO-d6) is consistent with the structure.

Workup

  1. temperatureThe mixture is heated
  2. waitat 25° C. for 16 hours
  3. stirringThe mixture is again stirred at 60° C. for 30 minutes
  4. waitat 25° C. for 3 hours
  5. waitto stand in the hood for 4 days
  6. customThe semi-solid precipitate is separated
  7. customby decanting the supernatant liquid

Sources & evidence

ORD record
ord-b194b15e65e9440aa68b5f91cf4bcd73
Source dataset
uspto-grants-2001_07
Patent number
US06255449B1

Reaction notes

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