Diethyl Ether → 1-Benzyl-3-iodoindazole

HRID 1935641Notes

Reaction equation

HRID 1935641 reaction equation
[H-].[Na+].[I:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][N:5]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)C>O1CCCC1.O>[CH2:13]([N:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4]([I:3])=[N:5]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178506566HCID 178506566, compound

Product 1

HCID 110676031-Benzyl-3-iodoindazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.49 g of 95% pure sodium hydride (59.0 mmol) were added in portions to a solution of 12.0 g (49.2 mmol) of 3-iodoindazole in 100 ml of anhydrous tetrahydrofuran under argon. After the mixture had been stirred at room temperature for 45 minutes, 7.02 ml (59.0 mmol) of benzyl bromide were added dropwise. The mixture was stirred overnight at room temperature, and diethyl ether and water were then added. The organic phase was washed with saturated sodium chloride solution, dried over magnesium sulphate and concentrated to dryness on a rotary evaporator. The excess benzyl bromide was separated off by bulb tube distillation. The distillation residue gave a product in the form of an oil which gradually crystallized.

Workup

  1. stirringThe mixture was stirred overnight at room temperature
  2. washThe organic phase was washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to dryness on a rotary evaporator
  5. customThe excess benzyl bromide was separated off by bulb tube
  6. distillationdistillation
  7. customThe distillation residue gave a product in the form of an oil which
  8. customgradually crystallized

Sources & evidence

ORD record
ord-f66eb12a0c0342269312d7ac88a7976e
Source dataset
uspto-grants-2002_05
Patent number
US06387940B1

Reaction notes

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