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

HRID 8401

反応式

HRID 8401 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 184318903,5-Dichlorophenyl-tert-butylsulfide収率 19%

試薬・触媒・溶媒 1

HCID 74236Tetrabutylammonium Bromide触媒

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-fc08a00bc9a040b3a45a8e40ce7d7458
出典データセット
uspto-grants-2006_08
特許番号
US07087764B2

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