Benzoyl Peroxide → tert-Butyl 3-(bromomethyl)-1H-pyrazole-1-carboxylate

HRID 2424415Notes

Reaction equation

HRID 2424415 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[N:3]=1.[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.CCOC(C)=O>[Br:14][CH2:1][C:2]1[CH:6]=[CH:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[N:3]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21035385tert-Butyl 3-methyl-1H-pyrazole-1-carboxylate

Product 1

HCID 23573257tert-Butyl 3-(bromomethyl)-1H-pyrazole-1-carboxylateYield 55.2%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

D5 (2 g, 10.97 mmol), N-bromosuccinimide (2.94 g, 16.46 mmol) and benzoyl peroxide (0.57 g, 1.65 mmol) were dissolved in carbon tetrachloride (40 ml) and heated to 80° C. for 3 h. The mixture was diluted with EtOAc (60 ml) and washed with saturated NaHCO3 solution and brine (100 ml each), dried (Na2SO4) and concentrated. Purification by column chromatography on silica (0-50% diethyl ether\40-60 pet. ether gradient) gave the title compound as a yellow oil (1.58 g). δH (CDCl3) 1.65 (9H, s), 4.49 (2H, s), 6.47 (1H, d), 8.03 (1H, d).

Workup

  1. washwashed with saturated NaHCO3 solution and brine (100 ml each)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification by column chromatography on silica (0-50% diethyl ether\40-60 pet. ether gradient)

Sources & evidence

ORD record
ord-08746af0ce3e4f208f0845de6f676224
Source dataset
uspto-grants-2011_06
Patent number
US07964602B2

Reaction notes

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