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

HRID 855578노트

반응식

HRID 855578 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-94316ccb9c33428b83a391269b59e010
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07262198B2

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