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

HRID 1375

Reaction equation

HRID 1375 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 (2×). 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 off.

Workup

  1. stirringthe reaction stirred at room temperature for 13 h
  2. extractionextracted with ether (2×)
  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-afbd95ad9dd44e7e978ad560efb01622
Source dataset
uspto-grants-1998_03
Patent number
US05723666

Linked notes

Loading…