Benzyl Bromide → 4-(2,4-Dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole

HRID 637593Notes

Reaction equation

HRID 637593 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:12])[C:10]=1[OH:11])=[O:5].C(N(CC)CC)C.[CH2:25](Br)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:3]=1[C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:12])[C:10]=1[O:11][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:5]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 178481842HCID 178481842, compound

Product 1

HCID 133217134-(2,4-Dichlorobenzoyl)-1-methyl-5-benzyloxypyrazoleYield 93%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a mixture of 1.50 g (0.0055 mol) of 4-(2,4-dichlorobenzoyl)-1-methyl-5-hydroxypyrazole, 0.56 g (0.0055 mol) of triethylamine and 30 ml of benzene was added 1.03 g (0.0061 mol) of benzyl bromide and the resulting mixture was heated under reflux for 2 hours with stirring. After cooling, precipitated triethyl amine hydrobromide was filtered off. The filtrate was concentrated under reduced pressure and was subjected to column chromatography (silica gel, using ethyl acetate/benzene 1:3 as an eluent) to give 1.79 g of the title compound 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole (yield: 93%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperatureAfter cooling
  4. customprecipitated triethyl amine hydrobromide
  5. filtrationwas filtered off
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-93814bf7ece5461c8ceb234868deca12
Source dataset
uspto-grants-1985_12
Patent number
US04557753

Reaction notes

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