tert-Butyl mercaptan → 3,5-Dichlorophenyl-tert-butylsulfide

HRID 8401

Reaction equation

HRID 8401 reaction equation
[OH-].[Na+].[C:3]([SH:7])([CH3:6])([CH3:5])[CH3:4].Cl[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:16][C:11]1[CH:10]=[C:9]([CH2:4][C:3]([S:7][C:3]([CH3:6])([CH3:5])[CH2:4][C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=2)([CH3:6])[CH3:5])[CH:14]=[C:13]([Cl:15])[CH:12]=1

Participants

5

Reactant 3

HCID 6387tert-Butyl mercaptanHCID 79501,3,5-TrichlorobenzeneHCID 14798Sodium Hydroxide

Product 1

HCID 184318903,5-Dichlorophenyl-tert-butylsulfideYield 19%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

To a solution of 4N sodium hydroxide (0.8 ml) was added tert-butylmercaptan (0.406 ml). The mixture was stirred for 15 minutes at room temperature. Tetra n-butylammonium bromide (322 mg, 1 mmol) and 1,3,5-trichlorobenzene (1) (1.8 g, 10 mmol) were added thereto. The reaction mixture was refluxed at 140° C. for 6.5 hours. The reaction mixture was poured into ice-water, extracted with ethylacetate, washed with water, dried over sodium sulphate, filtrated and concentrated under reduced pressure. The obtained residue was chromatographed twice on silica gel (SiO2 15 g, elution: n-hexane) to yield the objective (4) (138 mg). Yield 19%.

Workup

  1. temperatureThe reaction mixture was refluxed at 140° C. for 6.5 hours
  2. extractionextracted with ethylacetate
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltrated
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was chromatographed twice on silica gel (SiO2 15 g, elution: n-hexane)

Sources & evidence

ORD record
ord-fc08a00bc9a040b3a45a8e40ce7d7458
Source dataset
uspto-grants-2006_08
Patent number
US07087764B2

Linked notes

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