Acetonitrile → HCID 11436331, compound

HRID 2261230Notes

Reaction equation

HRID 2261230 reaction equation
FC(F)(F)S(O)(=O)=O.C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.[Br:24][C:25]1[CH:30]=[CH:29][C:28]([C:31](=[O:33])[CH3:32])=[CH:27][CH:26]=1.[CH3:34][C:35]#[N:36]>>[Br:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[O:33][C:35]([CH3:34])=[N:36][CH:32]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 4

HCID 6342Acetonitrile2×HCID 7466p-BromoacetophenoneHCID 62406Trifluoromethanesulfonic acidHCID 12217721Iodo benzene diacetate

Product 1

HCID 11436331HCID 11436331, compound

Procedure

Trifluoromethanesulfonic acid (6.6 ml) was added to a flask containing iodobenzene diacetate (12.2 g) and MeCN (200 ml) at rt. After 25 min. a solution of 4′-bromoacetophenone (5 g) in MeCN (50 ml) was added and the resultant mixture heated at reflux for 6 h. The reaction was allowed to cool to rt before the solvent was evaporated and the residue partitioned between saturated aqueous Na2CO3 (150 ml) and EtOAc (150 ml). The organic phase was washed with saturated brine (150 ml), dried (MgSO4) and evaporated to give an orange solid. The crude product was purified by column chromatography (silica gel, 50% EtOAc in hexane) to give the title compound (D15) as a pale yellow solid (3.5 g). LCMS electrospray (+ve) 239 (MH+).

Workup

  1. temperatureat reflux for 6 h
  2. customwas evaporated
  3. customthe residue partitioned between saturated aqueous Na2CO3 (150 ml) and EtOAc (150 ml)
  4. washThe organic phase was washed with saturated brine (150 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give an orange solid
  8. customThe crude product was purified by column chromatography (silica gel, 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-f573214dfaef4b1ab48ab1ec449326f6
Source dataset
uspto-grants-2010_12
Patent number
US07846922B2

Reaction notes

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