2-Pyrrolidone → HCID 12232698, compound

HRID 1658845Notes

Reaction equation

HRID 1658845 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][C:10]=1[CH2:18][S:19]([CH3:22])(=[O:21])=[O:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1CCCC1=O.C1CNC(=O)C1.[Br:35][Br-]Br>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH2:16][Br:35])=[CH:11][C:10]=1[CH2:18][S:19]([CH3:22])(=[O:20])=[O:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 120252-PyrrolidoneHCID 12232689HCID 12232689, compound

Product 1

HCID 12232698HCID 12232698, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 7.7 g. of 4'-benzyloxy-3'-methylsulfonylmethylacetophenone and 2.15 g. of 2-pyrrolidinone in 300 ml. of tetrahydrofuran is added 12.5 g. of pyrrolidinone hydrotribromide (PHT) and the stirring is continued for 56 hours at room temperature. The mixture is filtered and the filtrate concentrated in vacuo to give an oil which crystallizes upon standing. The crystals are redissolved in chloroform. The chloroform solution is washed with water, dried and concentrated to yield a solid which is recrystallized from acetonitrile to give 4'-benzyloxy-2-bromo-3'-methylsulfonylmethylacetophenone, m.p. 143°-144° C.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customto give an oil which
  4. customcrystallizes
  5. dissolutionThe crystals are redissolved in chloroform
  6. washThe chloroform solution is washed with water
  7. customdried
  8. concentrationconcentrated
  9. customto yield a solid which
  10. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-b7920cd5815245099b7d632e9f4e2c4f
Source dataset
uspto-grants-1976_06
Patent number
US03966770

Reaction notes

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