Phosphorus tribromide → Ethyl-3-bromomethyl-4-oxo-3-H-phthalazin-1-ylacetate

HRID 1607982Notes

Reaction equation

HRID 1607982 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[N:8]([CH2:17]O)[N:7]=1)[CH3:2].P(Br)(Br)[Br:21]>CCOCC>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[N:8]([CH2:17][Br:21])[N:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 14519538HCID 14519538, compound

Product 1

HCID 14519540Ethyl-3-bromomethyl-4-oxo-3-H-phthalazin-1-ylacetateYield 60.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of ethyl-3-hydroxymethyl-4-oxo-3-H-phthalazin-1-ylacetate (13.1 g), phosphorous tribromide (13.5 g) and anhydrous ether (250 ml) was stirred overnight at room temperature. It was then poured onto water (200 ml). The organic layer was collected, washed again with water (3×100 ml) and then dried over anhydrous sodium sulfate. The dried organic extract was evaporated to dryness and the resulting crude solid was purified by chromatography on silica gel, eluting with 95% CH2Cl2- 5% ethyl acetate (percents by volume) to obtain the title compound (yield: 9.8 g; m.p. 96° C.).

Workup

  1. additionIt was then poured onto water (200 ml)
  2. customThe organic layer was collected
  3. washwashed again with water (3×100 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. extractionThe dried organic extract
  6. customwas evaporated to dryness
  7. customthe resulting crude solid was purified by chromatography on silica gel
  8. washeluting with 95% CH2Cl2- 5% ethyl acetate (percents by volume)

Sources & evidence

ORD record
ord-7d97ea45a9d24bcca9aa6b9f3d86fd17
Source dataset
uspto-grants-1989_09
Patent number
US04868301

Reaction notes

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