Ammonium Chloride → 2-Bromobenzyl methyl sulfide
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
Product 1
Reagents, catalysts & solvents 1
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
- concentrationThe mixture was concentrated
- extractionextracted with ether The organic phase
- washwas washed with water
- dry with materialdried with MgSO4
- customAfter evaporation the crude product
- distillationwas distilled
Sources & evidence
- ORD record
- ord-4bc70bd1dd274ada8534b06842a83eca
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05223591
Reaction notes
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