Carbon tetrabromide → 4-(Bromomethyl)-1-(4-fluorophenyl)pyrrolidin-2-one

HRID 855578Notes

Reaction equation

HRID 855578 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:12][CH:11]([CH2:13]O)[CH2:10][C:9]2=[O:15])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:36]>N1C=CC=CC=1>[Br:36][CH2:13][CH:11]1[CH2:12][N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[C:9](=[O:15])[CH2:10]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 104656771-(4-Fluorophenyl)-4-(hydroxymethyl)pyrrolidin-2-one

Product 1

HCID 219354874-(Bromomethyl)-1-(4-fluorophenyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a cooled solution of 1-(4-fluorophenyl)-4-(hydroxymethyl)pyrrolidin-2-one (0.05 g, 0.25 mmol) in pyridine (3 ml) was added triphenylphosphine (0.130 g, 0.5 mmol). The solution was stirred and carbon tetrabromide (0.08 g, 0.25 mmol) was added in 3 separate portions. The reaction mixture was then allowed to warm to room temperature and stirred for three hours. The reaction was quenched with methanol and the solvent removed. The residue was dissolved in EtOAc (75 ml) and sequentially washed with ammonium chloride (sat, 2×25 ml) and water (25 ml). The organic layer was concentrated and purified using preparative tlc (1:1 EtOac:Hexanes) to yield 4-(bromomethyl)-1-(4-fluorophenyl)pyrrolidin-2-one (HNMR).

Workup

  1. customseparate portions
  2. stirringstirred for three hours
  3. customThe reaction was quenched with methanol
  4. customthe solvent removed
  5. dissolutionThe residue was dissolved in EtOAc (75 ml)
  6. washsequentially washed with ammonium chloride (sat, 2×25 ml) and water (25 ml)
  7. concentrationThe organic layer was concentrated
  8. custompurified

Sources & evidence

ORD record
ord-94316ccb9c33428b83a391269b59e010
Source dataset
uspto-grants-2007_08
Patent number
US07262198B2

Reaction notes

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