Bromine → HCID 67384609, compound

HRID 1471910Notes

Reaction equation

HRID 1471910 reaction equation
[CH2:1]([C:3]1[NH:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=1)[CH3:2].[Br:14]Br>C(Cl)Cl>[Br:14][C:4]1[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][NH:7][C:3]=1[CH2:1][CH3:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 1456373(5)-Ethyl-5(3)-phenylpyrazole

Product 1

HCID 67384609HCID 67384609, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-ethyl-3-phenyl-1H-pyrazole (10.0 g, 58.1 mmol) in DCM (150 mL) was added dropwise bromine (9.28 g, 58.1 mmol) at 0° C. The reaction was stirred at that temperature for 30 min and continued for 2 h at room temperature before quenched with aqueous Na2SO3 solution (10% wt, 10 mL). DCM was removed and the residue was extracted with EtOAc, washed with brine, dried over MgSO4, and concentrated. The residue was purified by silica gel column chromatography to give the title compound as a yellow liquid (9.5 g). LCMS m/z=250.9 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.22 (t, J=7.58 Hz, 3H), 2.66 (q, J=7.58 Hz, 2H), 7.40-7.56 (m, 3H), 7.82 (d, J=7.58 Hz, 2H), 13.15 (s, 1H).

Workup

  1. waitcontinued for 2 h at room temperature
  2. custombefore quenched with aqueous Na2SO3 solution (10% wt
  3. customDCM was removed
  4. extractionthe residue was extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-703703763ec2448ab486b9310b29e7bb
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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