Ammonium Chloride → 1-Bromo-2-[(methylsulfanyl)methyl]benzene

HRID 1588894Notes

Reaction equation

HRID 1588894 reaction equation
[CH3:1][S-:2].[Li+].[Br:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7]Br.[NH4+].[Cl-]>C(O)C.C1COCC1>[CH3:1][S:2][CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=1[Br:4]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 769652-Bromobenzyl bromideHCID 11018798HCID 11018798, compound

Product 1

HCID 41081381-Bromo-2-[(methylsulfanyl)methyl]benzeneYield 90.7%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a stirred solution of lithium thiomethoxide (82.19 mmol, generated from n-BuLi and methylmercaptan) in 130 ml of ethanol/THF (2:3) 2-bromobenzylbromide (12.54 g, 50.17 mmol) was added. After 1 h of reflux 30 ml of a saturated aqueous NH4Cl solution was added. The mixture was concentrated and extracted with ether The organic phase was washed with water and dried with MgSO4. After evaporation the crude product was distilled to give a clear liquid of o-bromobenzyl methyl sulfide 9.88 g (89%).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with ether The organic phase
  3. washwas washed with water
  4. dry with materialdried with MgSO4
  5. customAfter evaporation the crude product
  6. distillationwas distilled

Sources & evidence

ORD record
ord-4bc70bd1dd274ada8534b06842a83eca
Source dataset
uspto-grants-1993_06
Patent number
US05223591

Reaction notes

Loading…