Sulfuric Acid → 1-Bromo-2-[2-chloro-4-(methylsulphenyl)phenyl]acetylene

HRID 21458

Reaction equation

HRID 21458 reaction equation
[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[Br:13][C:14](Br)=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][C:17]=1[Cl:24].S(=O)(=O)(O)O>CO.C1(C)C=CC=CC=1>[Br:13][C:14]#[C:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][C:17]=1[Cl:24]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 66854Benzyltrimethylammonium hydroxideHCID 199317831,1-Dibromo-2-[2-chloro-4-(methylsulphenyl)phenyl]ethene

Product 1

HCID 199317681-Bromo-2-[2-chloro-4-(methylsulphenyl)phenyl]acetyleneYield 12,381.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent2×

Procedure

A suspension of Triton B (Reg Trade Mark, N-benzyltrimethylammonium hydroxide, 40% in methanol, 1.8 g) in toluene was added to a solution of 1,1-dibromo-2-[2-chloro-4-(methylsulphenyl)phenyl]ethene (0.96 g) in toluene. The mixture was stirred for 15 minutes. Sulphuric acid (2 m) was added and the resulting layers were separated. The organic layer was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromotography eluted with a mixture of hexane and dichloromethane to give 1-bromo-2-[2-chloro-4-(methylsulphenyl)phenyl]acetylene 90.78 g) as a yellow oil, NMR (CDCl3) 2.5 (s,3H), 7.05(d,1H), 7.2(s,1H), 7.35(d,1H).

Workup

  1. customthe resulting layers were separated
  2. washThe organic layer was washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromotography
  7. washeluted with a mixture of hexane and dichloromethane

Sources & evidence

ORD record
ord-f5d5be1f25384852af0050db91e2a0fa
Source dataset
uspto-grants-1995_06
Patent number
US05424276

Linked notes

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