4-Bromobenzyl bromide → HCID 19801019, compound

HRID 1646647Notes

Reaction equation

HRID 1646647 reaction equation
[O:1]1[CH:3]([CH2:4][CH:5]=[C:6]([CH3:8])[CH3:7])[C:2]1([CH:10]1[CH:15]([O:16][CH3:17])[CH:14]([OH:18])[CH2:13][CH2:12][C:11]1([CH2:20][S:21][CH3:22])[OH:19])[CH3:9].[Br:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=1>C(Cl)(Cl)Cl.[Ag]Br>[Br-:23].[Br:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][CH2:22][SH+:21][CH2:20][C:11]2([OH:19])[CH2:12][CH2:13][CH:14]([OH:18])[CH:15]([O:16][CH3:17])[CH:10]2[C:2]2([CH3:9])[O:1][CH:3]2[CH2:4][CH:5]=[C:6]([CH3:7])[CH3:8])=[CH:26][CH:25]=1

Participants

5

Reactant 2

HCID 685274-Bromobenzyl bromideHCID 19801008HCID 19801008, compound

Product 1

HCID 19801019HCID 19801019, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 66199Silver bromideCatalystHCID 6212ChloroformSolvent

Procedure

In chloroform (0.5 ml) were dissolved 2-(1,2-epoxy-1,5-dimethyl-4-hexenyl)-3-methoxy-1-methylthiomethyl-1,4-cyclohexanediol (200 mg) and 4-bromobenzyl bromide (756 mg). To the solution was added silver bromide (11.4 mg), and the mixture was stirred for 28 hours. Insolubles were filtered off, and the solvent was distilled off. The residue was pulverized by the addition of ether. The resulting powder was dissolved in methanol (2 ml). Insolubles were filtered off, then the solvent was distilled off under reduced pressure. The residue was pulverized by the addition of ether to give 1-(4-bromobenzyl)methylsulfoniomethyl-2-(1,2-epoxy- 1,5-dimethyl-4-hexenyl)-3-methoxy-1,4cyclohexanediol bromide (176 mg: yield 50%) as colorless powder.

Workup

  1. filtrationInsolubles were filtered off
  2. distillationthe solvent was distilled off
  3. additionThe residue was pulverized by the addition of ether
  4. dissolutionThe resulting powder was dissolved in methanol (2 ml)
  5. filtrationInsolubles were filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. additionThe residue was pulverized by the addition of ether

Sources & evidence

ORD record
ord-a9154d36c2a74164a79baf317f69f456
Source dataset
uspto-grants-1993_01
Patent number
US05180735

Reaction notes

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