Bromine → HCID 57416989, compound

HRID 2172153Notes

Reaction equation

HRID 2172153 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:3]=1.[Br:13]Br.OS([O-])=O.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.O>[Br:13][C:11]1[CH:10]=[N:9][N:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH:12]=1

Participants

7

Reactant 4

HCID 24408Bromine2×HCID 516892Sodium BicarbonateHCID 122381321-(4-chlorophenyl)-1H-pyrazoleHCID 23665763Sodium Bisulfite

Product 1

HCID 57416989HCID 57416989, compoundYield 66.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 1-(4-chlorophenyl)pyrazole (834 mg, 4.67 mmol) in acetic acid (10 mL) is treated with bromine (0.26 mL, 5.08 mmol). After stirring for 18 h, the solution is diluted with 40 mL water, and satd. aq. NaHSO3 solution is added until the bromine color had dissipated. Then, solid sodium bicarbonate is added until a neutral pH is obtained. This mixture is extracted with ethyl acetate (2×50 mL), and the extracts are washed with brine, combined, dried over MgSO4, filtered and evaporated. The solid residue is recrystallized from cyclohexane to afford pure product, 4-bromo-1-(4-chlorophenyl)-pyrazole (797 mg, 3.10 mmol, 66%). m.p. 75-76° C. (cyclohexane), 1H NMR (300 MHz, CDCl3): δ 7.89 (1H, s), 7.66 (1H, s), 7.57 (2H, d, J=9.0 Hz), 7.41 (2H, d, J=9.0 Hz). MS (ES+): m/e 261 (26), 259 (100), 257 (77).

Workup

  1. customis obtained
  2. extractionThis mixture is extracted with ethyl acetate (2×50 mL)
  3. washthe extracts are washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe solid residue is recrystallized from cyclohexane

Sources & evidence

ORD record
ord-c96494312071484d91c76d324b88916f
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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