N-bromobutanimide → HCID 13151502, compound

HRID 1648865Notes

Reaction equation

HRID 1648865 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:13])[CH2:9][CH2:10][CH:11]=[CH2:12])=[CH:4][CH:3]=1.[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][CH:11]([CH2:12][Br:14])[O:13]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 20481087HCID 20481087, compound

Product 1

HCID 13151502HCID 13151502, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 7.4 g of 1-(4-fluorophenyl)-4-penten-1-ol and 8.0 g of N-bromosuccinimide in 100 ml of chloroform is stirred at room temperature for 3 hours. The reaction mixture is then washed with water and dried over magnesium sulfate, and the solvent is distilled off under reduced pressure. The residue is purified by column chromatography on silica gel with chloroform eluant to give 9.8 g of 2-(4-fluorophenyl)-5-(bromomethyl)tetrahydrofuran as colorless oil, nD27 1.5218.

Workup

  1. washThe reaction mixture is then washed with water
  2. dry with materialdried over magnesium sulfate
  3. distillationthe solvent is distilled off under reduced pressure
  4. customThe residue is purified by column chromatography on silica gel with chloroform eluant

Sources & evidence

ORD record
ord-4732654209f34f90bd810354d96adf21
Source dataset
uspto-grants-1983_11
Patent number
US04414216

Reaction notes

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