Tetrahydrofuran → HCID 21430188, compound

HRID 1657879Notes

Reaction equation

HRID 1657879 reaction equation
[CH3:1][S:2][CH2:3][S:4]([CH3:6])=[O:5].O1CCCC1.[H-].[Na+].[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19]Br)=[CH:17][CH:16]=1>C(Cl)Cl>[Br:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][CH:3]([S:4]([CH3:6])=[O:5])[S:2][CH3:1])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 685274-Bromobenzyl bromideHCID 99129Methyl (methylsulfinyl)methyl sulfide

Product 1

HCID 21430188HCID 21430188, compoundYield 36.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.182 g of methyl methylthiomethyl sulfoxide was dissolved in 5 ml. of tetrahydrofuran, and under cooling with ice 229 mg (1.0 equivalent) of sodium hydride was added. The mixture was stirred for one hour. 1.91 g of p-bromobenzyl bromide (0.8 equivalent) was added, and the mixture was further stirred for 13 hours at room temperature. 50 ml. of methylene chloride was added, and the resulting precipitate was filtered. The filtrate was concentrated at reduced pressure, and subjected to column chromatography (silica gel, methylene chloride) to give 698 mg of methyl 2-(p-bromophenyl)-1-methylthioethyl sulfoxide in a yield of 36.5%.

Workup

  1. additionwas added
  2. stirringthe mixture was further stirred for 13 hours at room temperature
  3. filtrationthe resulting precipitate was filtered
  4. concentrationThe filtrate was concentrated at reduced pressure

Sources & evidence

ORD record
ord-3d0337e0401546bc991e8af088d04be7
Source dataset
uspto-grants-1976_06
Patent number
US03962281

Reaction notes

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