Phosphorus oxybromide → HCID 59234229, compound

HRID 2176839Notes

Reaction equation

HRID 2176839 reaction equation
[CH:1]1([CH2:4][N:5]2[CH:10]=[CH:9][C:8](O)=[C:7]([C:12]#[N:13])[C:6]2=[O:14])[CH2:3][CH2:2]1.P(Br)(Br)([Br:17])=O>CN(C=O)C>[Br:17][C:8]1[CH:9]=[CH:10][N:5]([CH2:4][CH:1]2[CH2:3][CH2:2]2)[C:6](=[O:14])[C:7]=1[C:12]#[N:13]

Participants

4

Reactant 2

HCID 24613Phosphorus oxybromideHCID 59234237HCID 59234237, compound

Product 1

HCID 59234229HCID 59234229, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of intermediate 3 (10.4 g, 54.67 mmol) in DMF (250 ml) was added phosphoric tribromide (31.3 g, 109.3 mmol) and the mixture was heated at 110° C. for 1.5 hours. After cooling in an ice bath the solution was partitioned between water and EtOAc. After three extractions with EtOAc the combined organic fractions were washed with brine, dried over MgSO4 and the solvent evaporated in vacuo. The crude product was purified by column chromatography (silica gel; DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate 5 (8.83 g, 64%).

Workup

  1. temperatureAfter cooling in an ice bath the solution
  2. customwas partitioned between water and EtOAc
  3. extractionAfter three extractions with EtOAc the combined organic fractions
  4. washwere washed with brine
  5. dry with materialdried over MgSO4
  6. customthe solvent evaporated in vacuo
  7. customThe crude product was purified by column chromatography (silica gel; DCM as eluent)
  8. customThe desired fractions were collected
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-0c4aa9b1f7eb46a9969c9deb504d38a9
Source dataset
uspto-grants-2015_06
Patent number
US09067891B2

Reaction notes

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