4-Bromomethyl-5-(4-bromo-phenyl)-3-methyl-isoxazole → HCID 66577235, compound

HRID 1528878Notes

Reaction equation

HRID 1528878 reaction equation
[CH:1]([Mg]Br)=[CH2:2].Br[CH2:6][C:7]1[C:8]([CH3:19])=[N:9][O:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1>C1COCC1.[Cu]I>[CH2:6]([C:7]1[C:8]([CH3:19])=[N:9][O:10][C:11]=1[C:12]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][CH:13]=1)[CH:1]=[CH2:2]

Participants

5

Reactant 2

HCID 665772234-Bromomethyl-5-(4-bromo-phenyl)-3-methyl-isoxazoleHCID 178418507HCID 178418507, compound

Product 1

HCID 66577235HCID 66577235, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

Copper(I) iodide (0.187 g, 0.98 mmol) was suspended in THF (43 mL) then cooled to −40° C. under N2 atmosphere. Vinylmagnesium bromide (1 M in THF, 9.74 mL, 9.74 mmol) was added over the course of 4 minutes and the reaction continued stirring for 18 minutes. Next, 4-bromomethyl-5-(4-bromo-phenyl)-3-methyl-isoxazole (2.15 g, 6.5 mmol) in THF (11 mL) was added over the course of 15 minutes. The reaction was placed in a −20° C. overnight. After warming the reaction was submitted to standard aqueous workup to afford the title compound.

Workup

  1. waitThe reaction was placed in a −20° C. overnight
  2. temperatureAfter warming the reaction

Sources & evidence

ORD record
ord-e614eb94e19f425dbee5ad27a0fa7641
Source dataset
uspto-grants-2015_07
Patent number
US09090573B2

Reaction notes

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