Cesium carbonate → 2-(4-Cyano-2-fluoro-phenoxymethyl)-benzoic acid methyl ester

HRID 1875773Notes

Reaction equation

HRID 1875773 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:17][O:18][C:19](=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26]Br>CC(C)=O>[CH3:17][O:18][C:19](=[O:28])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26][O:10][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 27829443-Fluoro-4-hydroxybenzonitrile

Product 1

HCID 670496082-(4-Cyano-2-fluoro-phenoxymethyl)-benzoic acid methyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-fluoro-4-hydroxy-benzonitrile (1.2 g, 8.7 mmol; CAS Reg. No. 405-04-9) in acetone (20 ml) was added cesium carbonate (4.2 g, 13.05 mmol) and 2-bromomethyl-benzoic acid methyl ester (2 g, 8.7 mmol; CAS Reg. No. 2417-73-4) and the resulting solution was heated to reflux for 12 h. The reaction mixture was filtered and evaporated in vacuo. The residue was purified by column chromatography over silica gel (8-10% ethyl acetate/n-hexane) to give the desired product as a yellow sticky solid (90%). MS (Turbo Spray): m/z=286.1 (M+H).

Workup

  1. temperature2417-73-4) and the resulting solution was heated
  2. temperatureto reflux for 12 h
  3. filtrationThe reaction mixture was filtered
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography over silica gel (8-10% ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-3acbcbf7656445f598b576d6a884e589
Source dataset
uspto-grants-2012_11
Patent number
US08309581B2

Reaction notes

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