Formaldehyde → HCID 86650269, compound

HRID 81586Notes

Reaction equation

HRID 81586 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH2:9][N+:10]([O-:12])=[O:11])[CH:3]=1.[CH2:13]=[O:14].CCN(CC)CC.[O:22]1CCOC[CH2:23]1>[Cl-].[Na+].O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([C:9]([N+:10]([O-:12])=[O:11])([CH2:13][OH:14])[CH2:23][OH:22])[CH:3]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 86650270HCID 86650270, compound

Product 1

HCID 86650269HCID 86650269, compound

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 4-bromo-1-fluoro-2-nitromethyl-benzene (7.75 g, 33.1 mmol), formaldehyde (35%, aqueous) (5.47 ml, 69.5 mmol) and Et3N (2.3 ml, 16.56 mmol) were stirred in 66 ml dioxane for 3 h. The solution was diluted with brine and extracted with TBME. The organic layer was washed with brine, dried with Na2SO4 and evaporated. The crude product was purified by chromatography on silica gel (heptane/EtOAc 3/1) to provide the title compound as a white solid. TLC (Hex: EE/2:1) Rf 0.24

Workup

  1. extractionextracted with TBME
  2. washThe organic layer was washed with brine
  3. dry with materialdried with Na2SO4
  4. customevaporated
  5. customThe crude product was purified by chromatography on silica gel (heptane/EtOAc 3/1)

Sources & evidence

ORD record
ord-a3da8e730200485a99f79889a511d60e
Source dataset
uspto-grants-2014_09
Patent number
US08846658B2

Reaction notes

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