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

HRID 271237ノート

反応式

HRID 271237 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-93f60da592cc408aa40bfb6a22ddf852
出典データセット
uspto-grants-2008_11
特許番号
US07452889B2

反応ノート

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