p-Toluenesulfonic acid → 2-Bromo-4-(dimethoxymethyl)-1-fluorobenzene

HRID 1985413Notes

Reaction equation

HRID 1985413 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[F:10])[CH:5]=[O:6].[C:11]1(C)C=CC(S(O)(=O)=O)=CC=1.[C:22](=[O:25])([O-])O.[Na+]>CO.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]([O:25][CH3:22])[O:6][CH3:11])[CH:7]=[CH:8][C:9]=1[F:10]

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 222608642-Bromo-4-(dimethoxymethyl)-1-fluorobenzene

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

5 g of 3-Bromo-4-fluorobenzaldehyde was dissolved in 40 ml of methanol, and 7.8 g trimethyl o-formate and 0.42 g of p-toluene sulfonic acid were added thereto, and the mixture was stirred at room temperature for 4 hours. The reaction solution was diluted with water and sodium hydrogencarbonate, and extracted with ethylacetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and evaporated, to give 6.2 g of the title compound.

Workup

  1. extractionextracted with ethylacetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-e253b2b629fd4e898e0069ba3e4c5bb6
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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