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

HRID 1426271

반응식

HRID 1426271 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-3b9d97be8a1c4beba2a87f3b50bcc943
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933095B2

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