Water → Bis(4-bromobenzyl)sulfide

HRID 2249292Notes

Reaction equation

HRID 2249292 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][SH:7])=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Br)=[CH:13][CH:12]=1.C(N(CC)CC)C.O>ClCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][S:7][CH2:15][C:14]2[CH:17]=[CH:18][C:11]([Br:10])=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 685274-Bromobenzyl bromideHCID 271218(4-Bromophenyl)methanethiol

Product 1

HCID 12328857Bis(4-bromobenzyl)sulfideYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.85 g (9.11 mmol) of 4-bromobenzylmercaptan in dry dichloromethane (30 ml) were added 2.72 g (10.9 mmol) of 4-bromobenzyl bromide and 2.31 g (22.8 mmol) of triethylamine in an atmosphere of argon, and the mixture was allowed to react at room temperature for 16 hours. To the solution was added water followed by extraction with ethyl acetate. The organic layer was washed with water and then concentrated under reduced pressure. The residue thus obtained was subjected to silica gel column chromatography for separation and purification. Elution with ethyl acetate-hexane (1:4) yielded 3.08 g (8.29 mmol) of bis(4-bromobenzyl)sulfide.

Workup

  1. customto react at room temperature for 16 hours
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. concentrationconcentrated under reduced pressure
  5. customThe residue thus obtained
  6. customwas subjected to silica gel column chromatography for separation and purification
  7. washElution with ethyl acetate-hexane (1:4)

Sources & evidence

ORD record
ord-5b2e5695cf634031a6e633db2c3b5008
Source dataset
uspto-grants-1991_08
Patent number
US05043142

Reaction notes

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