Hydrochloric Acid → HCID 67040236, compound

HRID 605263Notes

Reaction equation

HRID 605263 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12](F)=[C:11]([N+:16]([O-:18])=[O:17])[CH:10]=2)=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:27]([O:34][C:35]1[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.Cl>CN(C=O)C.C(OCC)(=O)C>[CH2:27]([O:34][C:35]1[CH:36]=[CH:37][C:38]([O:41][C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:19]=[CH:20][C:2]([Br:1])=[CH:3][CH:4]=3)=[CH:10][C:11]=2[N+:16]([O-:18])=[O:17])=[CH:39][CH:40]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7638MonobenzoneHCID 10796Cesium carbonateHCID 771890326901-29-5

Product 1

HCID 67040236HCID 67040236, compoundYield 8,639.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 247a (0.89 g, 2.63 mmol) was mixed with cesium carbonate (0.85 g, 2.63 mmol) and 4-benzyloxyphenol (0.53 g, 2.63 mmol) in DMF (10 mL) and stirred at room temperature a total of sixty hours. The reaction mixture was diluted with ethyl acetate (100 ml) and treated with 2N HCl (20 ml). The organic layer was separated and washed with 2N NaOH, 2, 10% sodium chloride and dried over anhydrous sodium sulfate. The drying agent was filtered and the solvent was evaporated under vacuum leaving the title compound as a yellow solid (118 g, 86%).

Workup

  1. customThe organic layer was separated
  2. washwashed with 2N NaOH, 2, 10% sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe drying agent was filtered
  5. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-506d78dd411f4eea999a64d00f18ea3a
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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