Ethanethiol → 2-Bromo-5,6-dihydro-5,5-dimethyl8-(ethylthio)-naphthalene

HRID 1289305Notes

Reaction equation

HRID 1289305 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.[CH2:15]([SH:17])[CH3:16].C(N(CC)CC)C>O1CCCC1.O.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]([CH3:14])([CH3:13])[CH2:7][CH:8]=[C:9]([S:17][CH2:15][CH3:16])[C:10]=2[CH:11]=1

Participants

7

Reactant 3

HCID 6343EthanethiolHCID 8471TriethylamineHCID 107533577-Bromo-4,4-dimethyl-1,2,3,4-tetrahydronaphthalen-1-one2×

Product 1

HCID 225715212-Bromo-5,6-dihydro-5,5-dimethyl8-(ethylthio)-naphthalene

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 1.03 g (4.1 mmol) of 7-bromo-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one (Compound G) in 30.0 mL of tetrahydrofuran, was added dropwise 0.49 g (0.85 mL, 7.8 mmol) of titaniumtetrachloride and the resulting solution stirred for 10 min. A solution of 35 mg (0.50 mL, 6.7 mmol) of ethanethiol and 0.54 g (0.75 mL, 5.4 mmol) of triethylamine in 10.0 mL of tetrahydrofuran was added and the reaction stirred at room temperature for 13 h. The mixture was diluted with water and extracted with ether (2x). The organic phase was washed with brine, dried over Na2SO4 and then concentrated in vacuo. Purification by flash chromatography (silica, 100% hexane) gave the title compound as an oil.

Workup

  1. stirringthe reaction stirred at room temperature for 13 h
  2. extractionextracted with ether (2x)
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography (silica, 100% hexane)

Sources & evidence

ORD record
ord-22ca545efc63483089e5cd6239054236
Source dataset
uspto-grants-1998_05
Patent number
US05747542

Reaction notes

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