Phosphorus tribromide → 3-[5-(bromomethyl)-4-chloro-2-fluorophenyl]-1,4-dimethyl-5-(trifluoromethyl)-1H-pyrazole

HRID 1378300Notes

Reaction equation

HRID 1378300 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[C:13]([CH3:14])=[C:12]([C:15]([F:18])([F:17])[F:16])[N:11]([CH3:19])[N:10]=2)=[CH:4][C:3]=1[CH2:20]O.P(Br)(Br)[Br:23]>C(OCC)C>[Br:23][CH2:20][C:3]1[C:2]([Cl:1])=[CH:7][C:6]([F:8])=[C:5]([C:9]2[C:13]([CH3:14])=[C:12]([C:15]([F:18])([F:17])[F:16])[N:11]([CH3:19])[N:10]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 229064162-chloro-5-[1,4-dimethyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzenemethanol

Product 1

HCID 229064283-[5-(bromomethyl)-4-chloro-2-fluorophenyl]-1,4-dimethyl-5-(trifluoromethyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 7.0 g of 2-chloro-5-[1,4-dimethyl-5-(trifluoromethyl)-1H-pyrazol-3-yl]-4-fluorobenzenemethanol in 200 mL of diethyl ether was added 30 mL of phosphorus tribromide and the mixture allowed to stir overnight. The reaction mixture was poured into ice water, the ether removed by concd in vacuo and the resultant solid collected by filtration. The solid was washed with water and air dried to give a quantitative yield of 3-[5-(bromomethyl)-4-chloro-2-fluorophenyl]-1,4-dimethyl-5-(trifluoromethyl)-1H-pyrazole: 1HNMR (CDCl3) δ 2.17 (t. 3H, 2.0 Hz), 4.07 (s, 3H), 4.64 (s, 2H), 7.30 (d, 1H, 9.5 Hz), 7.62 (d, 1H, 7.5 Hz); 19FNMR (CDCl3) δ -58.5 (s, 3F), -111.6 (s, 1F).

Workup

  1. customthe ether removed by concd in vacuo
  2. filtrationthe resultant solid collected by filtration
  3. washThe solid was washed with water and air
  4. customdried

Sources & evidence

ORD record
ord-25cce56120e64d46aaa124881c3daa16
Source dataset
uspto-grants-1997_09
Patent number
US05668088

Reaction notes

Loading…