Carbon tetrabromide → 1-benzyl-4-(bromomethyl)-3-nitro-1H-pyrazole

HRID 1426271ノート

反応式

HRID 1426271 の反応式
[C:1]([Br:5])(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([N:32]1[CH:36]=[C:35](CO)[C:34]([N+:39]([O-:41])=[O:40])=[N:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl>[CH2:25]([N:32]1[CH:36]=[C:35]([CH2:1][Br:5])[C:34]([N+:39]([O-:41])=[O:40])=[N:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 67963013(1-benzyl-3-nitro-1H-pyrazol-4-yl)methanol

生成物 1

HCID 679630121-benzyl-4-(bromomethyl)-3-nitro-1H-pyrazole

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Carbon tetrabromide (3.67 g, 11.1 mmol) and triphenylphosphine (2.43 mL, 11.1 mmol) were added to a solution of C3 (1.29 g, 5.53 mmol) in dichloromethane (150 mL), and the reaction was allowed to stir at RT for 18 hours. After being washed with water, the reaction mixture was dried over magnesium sulfate, filtered, and concentrated under reduced pressure. Silica gel chromatography (Gradient: 0% to 100% EtOAc in heptane) afforded C4 as a solid. Yield: 951 mg, 3.21 mmol, 58%. LCMS m/z 297.9 (M+1). 1H NMR (400 MHz, CDCl3) δ 4.60 (d, J=0.6 Hz, 2H), 5.32 (s, 2H), 7.28-7.32 (m, 2H), 7.36-7.41 (m, 3H), 7.52 (br s, 1H).

後処理

  1. washAfter being washed with water
  2. dry with materialthe reaction mixture was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-3b9d97be8a1c4beba2a87f3b50bcc943
出典データセット
uspto-grants-2015_01
特許番号
US08933095B2

反応ノート

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