Bromine → HCID 21837347, compound

HRID 1740100Notes

Reaction equation

HRID 1740100 reaction equation
[Br:1]Br.[CH2:3]([C:5]1[CH:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])[N:6]=1)[CH3:4]>C(O)(=O)C>[Br:1][C:9]1[C:5]([CH2:3][CH3:4])=[N:6][N:7]([C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH3:19])=[CH:14][C:13]=2[CH3:20])[C:8]=1[CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 24408BromineHCID 218373383,5-Diethyl-1-(2,4,6-trimethylphenyl)-1H-pyrazole

Product 1

HCID 21837347HCID 21837347, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 6.4 g (0.04 mol) of bromine in 20 mL of glacial acetic acid was added dropwise to a stirred solution of 9.00 g (37 mmol) of 3,5-diethyl-1-(2,4,6-trimethylphenyl)pyrazole in 100 mL of glacial acetic acid. After 1 hour at room temperature, the acetic acid was evaporated under reduced pressure and the residues were dissolved in ethyl acetate. This solution was washed with saturated sodium bicarbonate to remove residual acetic acid, dried with brine and magnesium sulfate, and was concentrated on the rotovap. The product was a tan solid (10.26 g, purification. 1H-NMR (CDCl3):0.92 (3H, t, J=7), 1.15 (3H, t, J=7), 1.86 (6H, s), 2.24 (3H, s), 2.32 (2H, q, J=7), 2.60 (2H, q, J=7), 6.82 (2H, s).

Workup

  1. customthe acetic acid was evaporated under reduced pressure
  2. dissolutionthe residues were dissolved in ethyl acetate
  3. washThis solution was washed with saturated sodium bicarbonate
  4. customto remove residual acetic acid
  5. dry with materialdried with brine and magnesium sulfate
  6. concentrationwas concentrated on the rotovap
  7. custom10.26 g, purification

Sources & evidence

ORD record
ord-27cd7952e45c4abfbacf4041ba50bc44
Source dataset
uspto-grants-1999_10
Patent number
US05968944

Reaction notes

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