Sodium hydride → HCID 59240049, compound

HRID 1673010Notes

Reaction equation

HRID 1673010 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[N:11]1[C:15]([OH:16])=[CH:14][C:13]([C:17]([F:20])([F:19])[F:18])=[N:12]1.[Br:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1>CN(C=O)C>[Br:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][O:16][C:15]2[N:11]([C:5]3[C:6]([Cl:10])=[CH:7][CH:8]=[CH:9][C:4]=3[Cl:3])[N:12]=[C:13]([C:17]([F:19])([F:20])[F:18])[CH:14]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 178516158HCID 178516158, compound

Product 1

HCID 59240049HCID 59240049, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At 0° C. NaH (60%, 400 mg, 10 mmol) was added to a stirred mixture of 1-(2,6-dichlorophenyl)-3-trifluoromethyl-1H-pyrazol-5-ol (1.5 g, 5 mmol) and 4-bromobenzyl bromide (1.5 g, 6 mmol) in dry DMF (20 mL), the resulting mixture was stirred at ambient temperature for 1 h, then quenched with aqueous NH4Cl at 0° C., extracted with EtOAc. The combined extracts were washed with H2O and brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by column chromatography (30% EtOAc/hexanes) to give 5-(4-bromobenzyloxy)-1-(2,6-dichlorophenyl)-3-trifluoromethyl-1H-pyrazole as a white solid (2.2 g, 94%). 1H-NMR (CDCl3): δ 7.47-7.41 (m, 4H), 7.36-7.33 (m, 1H), 7.17 (d, 2H), 5.93 (s, 1H), 5.08 (s, 2H), MS (ESI): 467[M+H]+.

Workup

  1. customAt 0° C
  2. customquenched with aqueous NH4Cl at 0° C.
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with H2O and brine
  5. dry with materialdried over Na2SO4
  6. customevaporated in vacuo
  7. customThe crude product was purified by column chromatography (30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-b278227c31a744f0bea25b344c421a65
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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