Diethyl Ether → 4-Bromo-2-fluoro-5-(methoxymethoxy)benzaldehyde

HRID 2236487Notes

Reaction equation

HRID 2236487 reaction equation
[Br:1][C:2]1[C:9]([OH:10])=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:11])[CH:3]=1.[CH2:12](Cl)[O:13][CH3:14].[H-].[Na+].CCOCC>CN(C)C=O>[Br:1][C:2]1[C:9]([O:10][CH2:12][O:13][CH3:14])=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:11])[CH:3]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 59300378HCID 59300378, compound

Product 1

HCID 593002954-Bromo-2-fluoro-5-(methoxymethoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

4-Bromo-2-fluoro-5-hydroxy-benzaldehyde (750 mg, 3.41 mmol) and MOMCl (545 mg, 6.82 mmol) were dissolved in anhydrous N,N-dimethylformamide (5 mL) and cooled to 0° C. NaH (160 mg, 60% suspension in mineral oil, 4 mmol) is then added. The resulting mixture is allowed to stir at room temperature for 1 h. Ether is then added and washed with H2O (3×20 mL) and brine. After dried over Na2SO4, the ether is removed and the residue is purified through chromatography to afford the desired MOM ether (700 mg, 78%).

Workup

  1. washwashed with H2O (3×20 mL) and brine
  2. dry with materialAfter dried over Na2SO4
  3. customthe ether is removed
  4. customthe residue is purified through chromatography
  5. customto afford the desired MOM ether (700 mg, 78%)

Sources & evidence

ORD record
ord-e1922472764e430ba5b08652c2d7bf12
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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