Phosphorus tribromide → 3-(Bromomethyl)-5-(4-chlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazole

HRID 729174Notes

Reaction equation

HRID 729174 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[N:11]=[C:10]([CH2:21]O)[CH:9]=2)=[CH:4][CH:3]=1.P(Br)(Br)[Br:24]>C1C=CC=CC=1>[Br:24][CH2:21][C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[N:11]=1

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 14871093HCID 14871093, compound

Product 1

HCID 148710973-(Bromomethyl)-5-(4-chlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of compound 3 (3.14 g, 10 mM) in benzene (100 ml) was added PBr3 (1.35 g, 5 mM) in benzene (10 ml) dropwise with stirring. The reaction mixture was refluxed 1 hr, cooled, poured into ice water (100 ml)and extracted with Et2O (2×100 ml). The combined organic layer was washed with 10% NaHCO3, dried (Na2SO4), filtered and concentrated to give a tan oilwhich crystallized on standing to afford compound 5, mp=88°-90° C., MS, (DCI) m/e 377 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed 1 hr
  2. temperaturecooled
  3. extractionextracted with Et2O (2×100 ml)
  4. washThe combined organic layer was washed with 10% NaHCO3
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a tan oilwhich
  9. customcrystallized

Sources & evidence

ORD record
ord-dedbf4f0047d4524b4d02a568617ea42
Source dataset
uspto-grants-1991_09
Patent number
US05051518

Reaction notes

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