Trityl chloride → 1H-Pyrazole, 3-bromo-1-(triphenylmethyl)-

HRID 32792

Reaction equation

HRID 32792 reaction equation
[Br:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.[C:7]1([C:13](Cl)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CCN(CC)CC.O.C(Cl)Cl>C(Cl)Cl>[Br:1][C:2]1[CH:6]=[CH:5][N:4]([C:13]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:3]=1

Participants

6

Reactant 4

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 21908982Water methylene chlorideHCID 178419412HCID 178419412, compound

Product 1

HCID 673126581H-Pyrazole, 3-bromo-1-(triphenylmethyl)-Yield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-bromo-pyrazole (2.0 g, 13.6 mmol) in anh. CH2Cl2 (40 mL), at r.t., under N2, were added triphenylmethyl chloride (4.17 g, 1.1 eq) and Et3N (2.1 mL, 1.1 eq). The reaction mixture was stirred at r.t. for 4 hr. It was poured into water/CH2Cl2. The phases were separated and the aqueous layer was further extracted with CH2Cl2 (2×30 mL). The combined organic extracts were dried over anh. Na2SO4, the solids were filtered and the solvent evaporated. The residue was purified by flash chromatography (silica gel, 100% CH2Cl2) to give the title compound as a white solid (3.39 g, 64%).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was further extracted with CH2Cl2 (2×30 mL)
  3. dry with materialThe combined organic extracts were dried over anh. Na2SO4
  4. filtrationthe solids were filtered
  5. customthe solvent evaporated
  6. customThe residue was purified by flash chromatography (silica gel, 100% CH2Cl2)

Sources & evidence

ORD record
ord-617ef31056a84a9fb21cf436620f582e
Source dataset
uspto-grants-2008_09
Patent number
US07427630B2

Linked notes

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