Methyl 4-(4-methoxyphenoxy)benzoate → HCID 67309982, compound

HRID 404706Notes

Reaction equation

HRID 404706 reaction equation
[B-]([S+](C)C)(F)(F)F.C[O:9][C:10]1[CH:26]=[CH:25][C:13]([O:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][CH:16]=2)=[CH:12][CH:11]=1>C(Cl)Cl>[CH3:22][O:21][C:19](=[O:20])[C:18]1[CH:17]=[CH:16][C:15]([O:14][C:13]2[CH:25]=[CH:26][C:10]([OH:9])=[CH:11][CH:12]=2)=[CH:24][CH:23]=1.[CH3:22][O:21][C:19](=[O:20])[C:18]1[CH:17]=[CH:16][C:15]([O:14][C:13]2[CH:25]=[CH:26][C:10]([OH:9])=[CH:11][CH:12]=2)=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 28911129Methyl 4-(4-methoxyphenoxy)benzoateHCID 71311438Dimethylsulfonio(trifluoro)boranuide

Product 1

HCID 67309982HCID 67309982, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron fluoride—dimethyl sulfide complex [CAS: 353-43-5] (15.64 ml, 148.67 mmol) was added dropwise to a stirred solution of methyl 4-(4′-methoxyphenoxy)benzoate [CAS: 38342-84-6] (1.28 g, 4.9 mmol) in DCM (100 ml) cooled in an ice-water bath under nitrogen atmosphere. The resulting mixture was stirred for 5 hours. The reaction mixture was washed with water and then extracted with DCM. The organic layer was separated and dried (Na2SO4) and the solvent was evaporated till dryness. The residue was purified by column chromatography (silica gel; 0-10% EtOAc/DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate D24 (0.89 g, 74%).

Workup

  1. temperaturecooled in an ice-water bath under nitrogen atmosphere
  2. washThe reaction mixture was washed with water
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was evaporated till dryness
  7. customThe residue was purified by column chromatography (silica gel; 0-10% EtOAc/DCM as eluent)
  8. customThe desired fractions were collected
  9. customevaporated in vacuo
  10. customto yield intermediate D24 (0.89 g, 74%)

Sources & evidence

ORD record
ord-2ea3cc90a304487b84680dcb189bad41
Source dataset
uspto-grants-2014_06
Patent number
US08748621B2

Reaction notes

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