(3-Bromopropyl)benzene → [3-(Methylsulfanyl)propyl]benzene

HRID 2246060Notes

Reaction equation

HRID 2246060 reaction equation
[CH3:1][S-:2].[Na+].[C:4]1([CH2:10][CH2:11][CH2:12]Br)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[C:4]1([CH2:10][CH2:11][CH2:12][S:2][CH3:1])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 12503(3-Bromopropyl)benzeneHCID 4378561Sodium methanethiolate

Product 1

HCID 22084628[3-(Methylsulfanyl)propyl]benzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methanethiolate (6 mmol, 0.42 g) and 3-phenylpropyl bromide (5 mmol, 1 g) in methanol were refluxed overnight. After removal of solvent, diethyl ether was added, washed with H2O and evaporated to give 3-phenylpropylmethyl sulfide. It was then reacted with equivalent amount of bromoacetic acid in acetonitrile (5 mL) at room temperature under N2 overnight, affording S-methyl-3-phenylpropylsulfoniumylacetic acid bromide as a white powder. It was then subjected to the general procedure 1 to give compound 585 as a white powder (0.75 g, 36% overall yield). Anal. (C12H19NaO7P2S.0.5 C2H5OH) C, H.

Workup

  1. customAfter removal of solvent, diethyl ether
  2. additionwas added
  3. washwashed with H2O
  4. customevaporated

Sources & evidence

ORD record
ord-5e408f5dd1f747e5a088f482db4c2648
Source dataset
uspto-grants-2010_03
Patent number
US07687482B2

Reaction notes

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