Iodine → HCID 57608017, compound

HRID 270097Notes

Reaction equation

HRID 270097 reaction equation
[Mg].II.Br[CH2:5][C:6]1[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=1[F:13].[CH2:14]([N:21]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>C(OCC)C>[CH2:14]([N:21]1[CH2:25][CH2:24][C:23]([CH2:5][C:6]2[CH:11]=[C:10]([Cl:12])[CH:9]=[CH:8][C:7]=2[F:13])([OH:26])[CH2:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 5

HCID 807IodineHCID 25517Ammonium ChlorideHCID 698901-Benzyl-3-pyrrolidinoneHCID 27736262-(Bromomethyl)-4-chloro-1-fluorobenzene2×HCID 5462224Magnesium

Product 1

HCID 57608017HCID 57608017, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a stirring suspension of magnesium strip (1.39 g, 57.06 mmol) in diethyl ether (10 mL) was added a crystal iodine followed by 0.5 mL of 2-(bromomethyl)-4-chloro-1-fluorobenzene under nitrogen. The reaction was initiated with a high intensity heat gun, then a solution of 2-(bromomethyl)-4-chloro-1-fluorobenzene (12.75 g, 57.06 mmol) in diethyl ether was added at such a speed that gentle reflux was maintained. After addition was complete the reaction mixture was kept on stirring at reflux for 3.5 h, cooled to room temperature and a solution of 1-benzylpyrrolidin-3-one (10.0 g, 57.06 mmol) in diethyl ether (20 mL) was added dropwise with vigorous stirring. After addition was complete the reaction mixture was left overnight at room temperature. This reaction mixture was treated with aqueous ammonium chloride (NH4Cl) solution and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulphate (Na2SO4), filtered, concentrated and the residue was purified by silica gel flash chromatography (0-2% methanol in dichloromethane, 0.2% ammonium hydroxide, NH4OH) to give the subtitled compound (650 mg).

Workup

  1. temperatureheat gun
  2. temperaturethat gentle reflux
  3. temperaturewas maintained
  4. additionAfter addition
  5. temperatureat reflux for 3.5 h
  6. additionAfter addition
  7. extractionextracted with ethyl acetate
  8. washThe organic layer was washed with water
  9. dry with materialdried over sodium sulphate (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customthe residue was purified by silica gel flash chromatography (0-2% methanol in dichloromethane, 0.2% ammonium hydroxide, NH4OH)

Sources & evidence

ORD record
ord-bdc88208e02f45d4b6962f92ff71c766
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Reaction notes

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