Bromine → HCID 67384969, compound

HRID 1471908Notes

Reaction equation

HRID 1471908 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:13]Br>C(O)(=O)C>[Br:13][C:4]1[C:3]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[C:2]([CH3:1])[NH:6][N:5]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 1396013-Methyl-4-phenylpyrazol

Product 1

HCID 67384969HCID 67384969, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-methyl-4-phenyl-1H-pyrazole (3.0 g, 18.96 mmol) in acetic acid (glacial, 100 mL) was added bromine (1.457 mL, 28.4 mmol) at room temperature. The reaction was stirred at room temperature for 2 h. After quenched with aqueous solution of Na2SO3 (10% wt aq., 10 mL), the reaction was concentrated and extracted with EtOAc, washed with brine, dried over MgSO4, and purified by silica gel column chromatography to give the title compound as yellow oil (2.8 g). LCMS m/z=236.9 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 2.26 (s, 3H), 7.24-7.54 (m, 5H), 13.13 (s, 1H).

Workup

  1. customAfter quenched with aqueous solution of Na2SO3 (10% wt aq., 10 mL)
  2. concentrationthe reaction was concentrated
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-8909991298544bfa8e02032afb069846
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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