Allyl Mercaptan → Methyl 4-bromo-2-(2-propenylsulphenylmethyl)benzoate

HRID 1492389Notes

Reaction equation

HRID 1492389 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12]Br)[CH:3]=1.[CH2:14]([SH:17])[CH:15]=[CH2:16].[O-]CC.[Na+].C(=O)(O)[O-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH2:12][S:17][CH2:14][CH:15]=[CH2:16])[CH:3]=1

Participants

6

Reactant 4

HCID 13367Allyl MercaptanHCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 22031079Methyl 4-bromo-2-(bromomethyl)benzoate

Product 1

HCID 18950273Methyl 4-bromo-2-(2-propenylsulphenylmethyl)benzoateYield 10%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

Methyl 4-bromo-2-bromomethylbenzoate (24.6 g) was added to a stirred mixture of allylmercaptan (70%, 9 g), sodium ethoxide (5.77 g) and tetrabutylammonium iodide (0.4 g) for 15 minutes. Cold sodium bicarbonate solution was added and the mixture extracted with ether. The extract was washed with brine, dried (magnesium sulphate) and evaporated to give methyl 4-bromo-2-(2-propenylsulphenylmethyl)benzoate (2.41 g), NMR (CDCl3) 3.05 (d,2H), 3.9 (s,3H), 4.0 (s,2H), 5.1 (m,2H), 5.75 (m,1H), 7.4 (d,1H), 7.5 (s,1H), 7.75 (d,1H).

Workup

  1. extractionthe mixture extracted with ether
  2. washThe extract was washed with brine
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated

Sources & evidence

ORD record
ord-d7cd7ea48f184acea3b6cd632c82a8b2
Source dataset
uspto-grants-1994_12
Patent number
US05374606

Reaction notes

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