Sodium Iodide → HCID 21196249, compound

HRID 1066847Notes

Reaction equation

HRID 1066847 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[CH2:4][OH:5].[H-].[Na+].[Cl:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]Br.[I-].[Na+]>CN(C)C=O.C(OCC)C>[F:1][C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[CH2:4][O:5][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][Cl:13]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 960701-Bromo-5-chloropentaneHCID 2773352(5-Bromo-2-fluorophenyl)methanol

Product 1

HCID 21196249HCID 21196249, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

In a 50 ml flask, under a nitrogen atmosphere, 2-fluoro-5-bromobenzyl alcohol (2.139 g, 10.4 mmol) was dissolved in N,N-dimethylformamide (25 ml). To this solution sodium hydride (60%, 625 mg, 15.6 mmol) was added and the resulting mixture was stirred for twenty minutes. To the reaction mixture 5-chloropentyl bromide was added and the resulting mixture was stirred for two hours at ambient temperature. The progress of the reaction was monitored by thin layer chromatography. Sodium iodide (3.127 g, 20.9 mmol) was added and the resulting mixture was stirred at ambient temperature for three hours. The reaction mixture was diluted with diethyl ether and washed seven times with brine. The solvents were removed in vacuo. The title intermediate was further purified by silica gel.

Workup

  1. stirringthe resulting mixture was stirred for two hours at ambient temperature
  2. stirringthe resulting mixture was stirred at ambient temperature for three hours
  3. washwashed seven times with brine
  4. customThe solvents were removed in vacuo
  5. customThe title intermediate was further purified by silica gel

Sources & evidence

ORD record
ord-25df30aba9454735ba0667a8eb6de570
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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