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

HRID 1599872Notes

Reaction equation

HRID 1599872 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 silica gel 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-00e3156301f14277867afe3577048ca7
Source dataset
uspto-grants-1998_04
Patent number
US05741896

Reaction notes

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