2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 69672992, compound

HRID 1751361Notes

Reaction equation

HRID 1751361 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.C(N(CC)CC)C.FC(F)(F)S(O[Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])(=O)=O.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:12][Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])=[CH:7][CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8471TriethylamineHCID 2724529Triisopropylsilyl trifluoromethanesulfonateHCID 101050696-Bromo-1-tetralone

Product 1

HCID 69672992HCID 69672992, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-bromo-1-tetralone (10.6 g, 47.1 mmol) in dichloromethane (145 mL) cooled to 0° C. were sequentially added triethylamine (12 mL, 86.1 mmol) and triisopropylsilyl trifluoromethanesulfonate (15.3 mL, 56.7 mmol). After stirring for ten minutes, the ice bath was removed and the reaction was allowed to warm to room temperature for 30 minutes. The reaction was diluted with 1:1 ethyl acetate:hexanes and the organic layer was washed with water and brine. The organics were dried (MgSO4), concentrated, and the resulting material was used without further purification. The crude enolsilane was dissolved in tetrahydrofuran (470 mL) and cooled to 0° C. To the solution was added solid 2,3-dichloro-5,6-dicyanobenzoquinone (16 g, 70.5 mmol) and the reaction was warmed to room temperature. After 30 minutes the reaction was concentrated and the crude material was purified by flash column chromatography (hexanes) to afford (6-bromonaphthalen-1-yloxy)triisopropylsilane (17.1 g, 96% over 2 steps).

Workup

  1. customthe ice bath was removed
  2. additionThe reaction was diluted with 1:1 ethyl acetate
  3. washhexanes and the organic layer was washed with water and brine
  4. dry with materialThe organics were dried (MgSO4)
  5. concentrationconcentrated
  6. customthe resulting material was used without further purification
  7. dissolutionThe crude enolsilane was dissolved in tetrahydrofuran (470 mL)
  8. temperaturecooled to 0° C
  9. temperaturethe reaction was warmed to room temperature
  10. concentrationAfter 30 minutes the reaction was concentrated
  11. customthe crude material was purified by flash column chromatography (hexanes)

Sources & evidence

ORD record
ord-31ad0114ccce462d966c04b63fc708d2
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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