Bromine → Diethyl 2-bromo-3,4,5-trimethoxyphenylphosphonate

HRID 48083Notes

Reaction equation

HRID 48083 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18])[CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12].C([O-])(O)=O.[Na+]>C(O)(=O)C>[Br:1][C:6]1[C:5]([O:4][CH3:3])=[C:10]([O:11][CH3:12])[C:9]([O:13][CH3:14])=[CH:8][C:7]=1[P:15](=[O:22])([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 21185491Diethyl 3,4,5-trimethoxyphenylphosphonate

Product 1

HCID 21185533Diethyl 2-bromo-3,4,5-trimethoxyphenylphosphonate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (10 mmol) in 10 mL of acetic acid is added dropwise to a solution of ester 11 (10 mmol) in 10 mL of acetic acid cooled by an ice water bath. After the red color of the resulting mixture is discharged, the mixture is poured into saturated NaHCO3 (100 mL) and extracted with ethyl acetate (3×100 mL). The combined organic phases are washed with 100 mL portions of 5% NaHCO3 until no further gas evolution is apparent. The organic phases are then washed with brine (100 mL), dried over anhydrous MgSO4, and concentrated in vacuo. The mixture is purified by flash chromatography to give the product as a pale yellow solid.

Workup

  1. temperaturecooled by an ice water bath
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washThe combined organic phases are washed with 100 mL portions of 5% NaHCO3 until no further gas evolution
  4. washThe organic phases are then washed with brine (100 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe mixture is purified by flash chromatography

Sources & evidence

ORD record
ord-d34af63acb464c238739b2729f02545b
Source dataset
uspto-grants-2004_03
Patent number
US06702705B1

Reaction notes

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