Water → HCID 59442619, compound

HRID 657515Notes

Reaction equation

HRID 657515 reaction equation
[Br:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][N:3]=1.[H-].[Na+].Br[CH2:16][CH:17]1[CH2:19][CH2:18]1.O>CN(C=O)C>[Br:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]([CH2:16][CH:17]2[CH2:19][CH2:18]2)[N:3]=1.[Br:1][C:2]1[N:3]([CH2:16][CH:17]2[CH2:19][CH2:18]2)[N:4]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 178419310HCID 178419310, compound

Product 2

HCID 59442619HCID 59442619, compoundHCID 59442697HCID 59442697, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.7 g of 3-bromo-5-phenyl-1H-pyrazole were dissolved in 50 ml of anhydrous DMF, 0.74 g of sodium hydride and 4.1 g of bromomethylcyclopropane were added and the mixture was allowed to stand for 17 h at room temperature. The reaction mixture was then treated with 1 ml of water and the volatile constituents were removed in vacuo. Chromatography on reversed phase silica gel yielded 1.4 g of 3-bromo-1-cyclopropylmethyl-5-phenyl-1H-pyrazole and 2.7 g of 5-bromo-1-cyclopropylmethyl-3-phenyl-1H-pyrazole as viscous oils.

Workup

  1. customthe volatile constituents were removed in vacuo

Sources & evidence

ORD record
ord-2c215584cfb84e72895df359fa37af9b
Source dataset
uspto-grants-2011_12
Patent number
US08076324B2

Reaction notes

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