Cesium carbonate → Methyl 4-((3-((phenylamino)methyl)phenoxy)methyl)benzoate

HRID 1497983Notes

Reaction equation

HRID 1497983 reaction equation
[C:1]1([NH:7][CH2:8][C:9]2[CH:10]=[C:11]([OH:15])[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:22][O:23][C:24](=[O:33])[C:25]1[CH:30]=[CH:29][C:28]([CH2:31]Br)=[CH:27][CH:26]=1>CN(C=O)C>[C:1]1([NH:7][CH2:8][C:9]2[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=2)[O:15][CH2:31][C:28]2[CH:29]=[CH:30][C:25]([C:24]([O:23][CH3:22])=[O:33])=[CH:26][CH:27]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 213213663-(Anilinomethyl)phenol

Product 1

HCID 86720705Methyl 4-((3-((phenylamino)methyl)phenoxy)methyl)benzoateYield 19.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-((phenylamino)methyl)phenol (398 mg, 2 mmol) and cesium carbonate (651 mg, 2 mmol) in anhydrous DMF (8 mL) was added methyl-4-(bromomethyl)benzoate (481 mg, 2.1 mmol). The resulting mixture was stirred for 22 hours at room temperature, after which time the solvent was removed in vacuo. The residue was partitioned between dichloromethane (30 mL) and water (10 mL). The mixture was passed through a phase separator, washed with dichloromethane and solvent was removed in vacuo to afford a brown oil. The crude material was purified by silica gel chromatography eluting with 25% ethyl acetate in iso-hexane to afford the title compound as a yellow oil (133 mg, 19%).

Workup

  1. customafter which time the solvent was removed in vacuo
  2. customThe residue was partitioned between dichloromethane (30 mL) and water (10 mL)
  3. washwashed with dichloromethane and solvent
  4. customwas removed in vacuo
  5. customto afford a brown oil
  6. customThe crude material was purified by silica gel chromatography
  7. washeluting with 25% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-a5b668381e5f47dc97232389c7ad3527
Source dataset
uspto-grants-2015_12
Patent number
US09199980B2

Reaction notes

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