2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Ethyl (5-fluoronaphthalen-1-yl)acetate

HRID 331248Notes

Reaction equation

HRID 331248 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH:6]=[C:7]2[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C1C=CC=CC=1.[OH-].[Na+]>[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 86641634Ethyl (5-fluoro-3,4-dihydronaphthalen-1-yl)acetate

Product 1

HCID 86641635Ethyl (5-fluoronaphthalen-1-yl)acetateYield 34.8%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of ethyl (5-fluoro-3,4-dihydronaphthalen-1-yl)acetate (16.4 g) in benzene (500 mL) was DDQ (2,3-dichloro-5,6-dicyanobenzoquinone)(21.5 g), and the mixture was stirred with heating for 3 hr. After cooling, the precipitated solid was dissolved in 1N sodium hydroxide, and the mixture was extracted with toluene. The extract was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give ethyl (5-fluoronaphthalen-1-yl)acetate (5.66 g).

Workup

  1. temperaturewith heating for 3 hr
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with toluene
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-be1c240088864f06b1c9993f86e5a1f0
Source dataset
uspto-grants-2014_11
Patent number
US08877779B2

Reaction notes

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