4,6-Dibromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene → 6-Bromo-1,2,3,4-tetrahydro-1,1-dimethyl-4-thioacetylnaphthalene

HRID 1221

Reaction equation

HRID 1221 reaction equation
Br[CH:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Br:12])[CH:10]=2)[C:5]([CH3:14])([CH3:13])[CH2:4][CH2:3]1.[C:15]([O-])(=[S:17])[CH3:16].[K+]>C1COCC1>[Br:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[C:5]([CH3:14])([CH3:13])[CH2:4][CH2:3][CH:2]2[C:15](=[S:17])[CH3:16]

Participants

4

Reactant 2

HCID 196949614,6-Dibromo-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene2×HCID 23670855Potassium ethanethioate

Product 1

HCID 196949646-Bromo-1,2,3,4-tetrahydro-1,1-dimethyl-4-thioacetylnaphthalene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Employing the above-described procedure for the conversion of 6-bromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene naphthalene (Compound F) to the dibromonaphthalene derivative (Compond I), 3.5 g (14.6 mmol) of (Compound F), 2.86 g (16.1 mmol) of N-bromosuccinimide and 150 mg (0.62 mmol ) of benzoylperoxide gave crude 4,6-dibromo-1,2,3,4-tetrahydro-1,1-dimethylnaphthalene (Compound I). To a solution of this crude dibromonaphthalene derivative (Compound I) in 50 ml of THF was added 5.38 g (47.1 mmol) of potassium thioacetate. The mixture was refluxed for 6 hours under argon atmosphere, filtered through celite and concentrated in vacuo. Purification by chromatography (silica, 10% EtOAc-hexane) yielded the title compound as red oil.

Workup

  1. temperatureThe mixture was refluxed for 6 hours under argon atmosphere
  2. filtrationfiltered through celite and
  3. concentrationconcentrated in vacuo
  4. customPurification by chromatography (silica, 10% EtOAc-hexane)

Sources & evidence

ORD record
ord-8ad41e85bae94573960b3d36e878b3e1
Source dataset
uspto-grants-1998_03
Patent number
US05723620

Linked notes

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