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

HRID 1426271Notes

Reaction equation

HRID 1426271 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-3b9d97be8a1c4beba2a87f3b50bcc943
Source dataset
uspto-grants-2015_01
Patent number
US08933095B2

Reaction notes

Loading…