Benzyl Bromide → HCID 66890793, compound

HRID 253270Notes

Reaction equation

HRID 253270 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([OH:14])[C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:14][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 45115824Methyl 3-fluoro-5-hydroxy-4-methoxybenzoate

Product 1

HCID 66890793HCID 66890793, compoundYield 67.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-fluoro-5-hydroxy-4-(methyloxy)benzoate (3.63 g, 18.1 mmol.) in DMF (25 mL) was added cesium carbonate (8.9 g, 27.2 mmol.) followed by benzyl bromide (2.8 mL, 23.6 mmol.) and the mixture was stirred at room temperature over 12 hours. The mixture was then partitioned with ethyl ether and water and the organic phase washed with water (3×) then saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. Filtration and concentration followed by purification of the residue by silica gel flash chromatography using 50% hexanes in chloroform as eluent afforded methyl 3-fluoro-4-(methyloxy)-5-[(phenylmethyl)oxy]benzoate (3.54 g, 67% yield) as a colorless solid after concentration of the pure fractions and drying in vacuo.

Workup

  1. customThe mixture was then partitioned with ethyl ether and water
  2. washthe organic phase washed with water (3×)
  3. dry with materialsaturated aqueous sodium chloride and dried over anhydrous magnesium sulfate
  4. filtrationFiltration and concentration
  5. customfollowed by purification of the residue by silica gel flash chromatography

Sources & evidence

ORD record
ord-bfeaf47db83e4b0cb2231d0d7a8bf4ab
Source dataset
uspto-grants-2011_01
Patent number
US07872014B2

Reaction notes

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