HCID 233935, compound → HCID 18984759, compound

HRID 1439902Notes

Reaction equation

HRID 1439902 reaction equation
F[B-](F)(F)F.[O:6]=[N+:7]=[O:8].[Cl:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH2:15][CH2:14][CH2:13]2>ClCCl>[Cl:9][C:10]1[CH:11]=[C:12]2[C:17]([CH2:16][CH2:15][CH2:14][CH2:13]2)=[C:18]([N+:7]([O-:8])=[O:6])[CH:19]=1

Participants

4

Reactant 2

HCID 233935HCID 233935, compoundHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 18984759HCID 18984759, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 85% nitronium tetrafluoroborate (6.19 g, 39.6 mmol) in dichloromethane (60 mL) was added dropwise a solution of 6-chlorotetralin (6.0 g, 36 mmol) in dichloromethane (60 mL) over 15 min at 0° C. The mixture was stirred for 40 min at 0° C. and quenched by addition of ice-water (100 mL). The organic layer was separated, washed with water, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography with 30:1~4:1 hexane/toluene to give 3.83 g of the title compound (54%): 1H NMR (CDCl3) δ7.65 (d, 1H, J=2.3 Hz), 7.30 (d, 1H, J=8.9 Hz), 2.90 (m, 4H), 1.76 (m, 4H).

Workup

  1. customquenched by addition of ice-water (100 mL)
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography with 30:1~4:1 hexane/toluene

Sources & evidence

ORD record
ord-0f4d707424aa4327aa634e7897ba5f8f
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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