Methyl iodide → 5-Bromo-3-fluoro-2-methoxybenzaldehyde

HRID 2373819Notes

Reaction equation

HRID 2373819 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:12]([O-])([O-])=O.[Cs+].[Cs+].IC>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([F:11])[C:5]([O:10][CH3:12])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 27792765-Bromo-3-fluoro-2-hydroxybenzaldehyde

Product 1

HCID 229260135-Bromo-3-fluoro-2-methoxybenzaldehydeYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-Bromo-3-fluoro-2-hydroxy-benzaldehyde (2.0 g, 9.13 mmol), in DMF (10 mL) was added Cs2CO3 (3.56 g, 10.95 mmol) and iodomethane (2.59 g, 18.26 mmol) and heated at 70° C. for 6 h. Reaction mixture was diluted with EtOAc (25 mL) and filtered, filtrate was washed with water, brine and dried over Na2SO4. Solvent was removed under reduced pressure and silicagel column chromatography (EtOAc:Hex, 1:3) gave pure 5-Bromo-3-fluoro-2-methoxy-benzaldehyde (2.0 g).

Workup

  1. customReaction mixture
  2. filtrationfiltered
  3. washfiltrate was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. customSolvent was removed under reduced pressure and silicagel column chromatography (EtOAc:Hex, 1:3)

Sources & evidence

ORD record
ord-93ba25c59e9046bcb3a05c670a5bcbfe
Source dataset
uspto-grants-2008_12
Patent number
US07459472B2

Reaction notes

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