Phosphorus tribromide → 5-Bromomethyl-1-(2,6-dichlorophenyl)-4-isopropyl-1H-pyrazole

HRID 1689764Notes

Reaction equation

HRID 1689764 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:13]([CH2:14]O)=[C:12]([CH:16]([CH3:18])[CH3:17])[CH:11]=[N:10]1.P(Br)(Br)[Br:20]>C(Cl)Cl.O>[Br:20][CH2:14][C:13]1[N:9]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])[N:10]=[CH:11][C:12]=1[CH:16]([CH3:18])[CH3:17]

Participants

5

Reactant 2

HCID 24614Phosphorus tribromideHCID 57443256(1-(2,6-dichlorophenyl)-4-isopropyl-1H-pyrazol-5-yl)methanol

Product 1

HCID 574433665-Bromomethyl-1-(2,6-dichlorophenyl)-4-isopropyl-1H-pyrazoleYield 10.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-(2,6-dichlorophenyl)-4-isopropyl-1H-pyrazol-5-yl)methanol (4.0 g, 0.014 mol) in CH2Cl2 (50 ml) is added phosphorus tribromide (5.69 g, 0.021 mol) at 0° C. Stir the mixture for 3 h at room temperature. Dilute with water and extract with ethyl acetate. Concentrate under reduced pressure, to give crude product, which is purified by column chromatography over silica gel eluting with 7:3 hexane/ethyl acetate to give 0.50 g (10%) of the title compound. ES/MS m/e (81Br) 348.93 [M+H]+.

Workup

  1. extractionextract with ethyl acetate
  2. concentrationConcentrate under reduced pressure
  3. customto give crude product, which
  4. customis purified by column chromatography over silica gel eluting with 7:3 hexane/ethyl acetate

Sources & evidence

ORD record
ord-1ae9b954096b4a1c931050b808c8555c
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

Loading…