Bromine → HCID 178478024, compound

HRID 259695Notes

Reaction equation

HRID 259695 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:12]=[CH:11][NH:10][N:9]=1.[Br:13]Br>C(O)(=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([Br:13])=[CH:11][NH:10][N:9]=1

Participants

5

Reactant 2

HCID 24408Bromine2×HCID 178478013HCID 178478013, compound

Product 1

HCID 178478024HCID 178478024, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent3×HCID 6344DichloromethaneSolvent

Procedure

3.5 g of 3-(2-chlorophenyl)-1H-pyrazole, prepared as in Example 9, are dissolved, at room temperature and with stirring, in 20 ml of acetic acid. A solution of 3.76 g (0.0235 mol) of bromine in 20 ml of acetic acid is then run dropwise into the reaction mixture. Stirring is maintained for 1 hour at room temperature and then the acetic acid and the excess bromine are driven off under reduced pressure. The residue is taken up in methylene chloride and this organic solution is washed with an aqueous bicarbonate solution, then with water and then dried over MgSO4 before being concentrated to dryness. The residue is recrystallised from pentane. 3.3 g (0.0128 mol) of 3-(2'-chlorophenyl)-4-bromo-1H-pyrazole are obtained, which melts at 80° C. (yield 65%) (compound 94),

Workup

  1. dissolutionare dissolved, at room temperature
  2. washthis organic solution is washed with an aqueous bicarbonate solution
  3. dry with materialwith water and then dried over MgSO4
  4. concentrationbefore being concentrated to dryness
  5. customThe residue is recrystallised from pentane

Sources & evidence

ORD record
ord-8b0af1d9dcda439abcc48a345df6369d
Source dataset
uspto-grants-1996_06
Patent number
US05523280

Reaction notes

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