Hydrochloric Acid → 7-tert-butyl-2,3-dihydro-3,3-dimethylbenzothiophene

HRID 1488577노트

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HRID 1488577 반응식
[CH:1]([S:5][C:6]1[C:11]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:10][CH:9]=[CH:8][C:7]=1Br)=[C:2]([CH3:4])[CH3:3].[PH2](O)=O.C(N(CC)CC)C.Cl>O1CCOCC1.[Cl-].[Na+].O>[CH3:3][C:2]1([CH3:4])[CH2:1][S:5][C:6]2[C:11]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:10][CH:9]=[CH:8][C:7]1=2

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 4124402Phosphinic AcidHCID 22905880HCID 22905880, 화합물

생성물 1

HCID 107041827-tert-butyl-2,3-dihydro-3,3-dimethylbenzothiophene

시약·촉매·용매 2

HCID 312751,4-Dioxane용매2회HCID 57417360Sodium chloride; water용매

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온도
24 °C

실험 절차

A solution of 2-bromo-6-tert-butylphenyl isobutenyl thioether (600 mg, 2.07 mmol), 90% hypophosphorous acid (4.4 g, 60 mmol), and triethylamine (8.4 mL, 60 mmol) in dioxane (30 mL) is deoxygenated by bubbling with N2 for 20 min. The solution is then heated under N2 to reflux, and a solution of azo-bis-isobutyrylnitrile (205 mg, 1.04 mmol) in deoxygenated dioxane (2 mL) is added in 0.2-mL portions over 3 h. The reaction is allowed to cool to 24° C., and 1N HCl (40 mL) and brine (30 mL) are added. The mixture is extracted with Et2O (3×50 mL), and the ethereal layers are back extracted with 1N NaOH (40 mL). The organic phase is dried (MgSO4), filtered and evaporated to a yellow oil. Kugelrohr distillation provides 3,3-dimethyl-7-tert-butyl-2,3-dihydrobenzo[b]thiophene as a colorless oil.

후처리

  1. customby bubbling with N2 for 20 min
  2. temperatureThe solution is then heated under N2
  3. temperatureto reflux
  4. extractionThe mixture is extracted with Et2O (3×50 mL)
  5. extractionthe ethereal layers are back extracted with 1N NaOH (40 mL)
  6. dry with materialThe organic phase is dried (MgSO4)
  7. filtrationfiltered
  8. customevaporated to a yellow oil
  9. distillationKugelrohr distillation

출처 및 근거

ORD 기록
ord-e06977f8af2744b9acf9f84ff78c9807
출처 데이터셋
uspto-grants-1997_10
특허 번호
US05674891

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