Thiophenol → 4,4-Dimethyl-7-bromo-1-phenylthio-3,4-dihydronaphthalene

HRID 24571

Reaction equation

HRID 24571 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:14])([CH3:13])[CH2:7][CH2:8][C:9]2=O)=[CH:4][CH:3]=1.C1COCC1.[C:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>[Ti](Cl)(Cl)(Cl)Cl.O>[CH3:13][C:6]1([CH3:14])[C:5]2[C:10](=[CH:11][C:2]([Br:1])=[CH:3][CH:4]=2)[C:9]([S:26][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:8][CH2:7]1

Participants

7

Reactant 4

HCID 7969ThiophenolHCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 107533577-Bromo-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-one2×

Product 1

HCID 158960184,4-Dimethyl-7-bromo-1-phenylthio-3,4-dihydronaphthalene

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolvent

Procedure

To a stirred solution of 4,4-dimethyl-7-bromo-3,4-dihydronaphthalen-1(2H)one (Compound G, 1.48 g, 5.9 mmol), titanium tetrachloride (1.09 g, 5.7 mmol) and THF (10 mL) was added a mixture of thiophenol (660 mg, 6 mmol), triethylamine (1.16 g, 11.5 mmol) and THF (20 mL) via an addition funnel at ambient temperature. The mixture was stirred for 5 h, and water (10 mL) was added, extracted with ether (3×50 mL). The combined organic layer was washed successively with water (10 mL), 10% NaHCO3 (10 mL) and brine (10 mL). The organic layer was dried (MgSO4) and the solvent distilled off at reduced pressure. After silicagel chromatography the title compound was obtained as a colorless oil

Workup

  1. extractionextracted with ether (3×50 mL)
  2. washThe combined organic layer was washed successively with water (10 mL), 10% NaHCO3 (10 mL) and brine (10 mL)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. distillationthe solvent distilled off at reduced pressure

Sources & evidence

ORD record
ord-60e46af075ba419ea97873f93ff81cab
Source dataset
uspto-grants-2005_02
Patent number
US06855832B2

Linked notes

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