Triethylamine → 2-Ethoxy-1,8-difluorophenanthrene-9,10-dione

HRID 718503Notes

Reaction equation

HRID 718503 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([F:21])=[C:6]([CH:19]=[O:20])[C:7]([C:10]2[C:11]([CH:17]=[O:18])=[C:12]([F:16])[CH:13]=[CH:14][CH:15]=2)=[CH:8][CH:9]=1)[CH3:2].C(N(CC)CC)C>[Br-].C([N+]1C(C)=C(CCO)SC=1)C.CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]2[C:10]3[C:11](=[C:12]([F:16])[CH:13]=[CH:14][CH:15]=3)[C:17](=[O:18])[C:19](=[O:20])[C:6]=2[C:5]=1[F:21])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 866960744-Ethoxy-3,3'-difluoro-[1,1'-biphenyl]-2,2'-dicarboaldehyde

Product 1

HCID 680105882-Ethoxy-1,8-difluorophenanthrene-9,10-dioneYield 703.9%

Reagents, catalysts & solvents 2

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromideCatalystHCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, a DMF (50 mL) solution of compound (85) (10.0 g, 3.45 mmol), 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazole-3-iumbromide (1.74 g, 6.89 mmol) and triethylamine (1.05 g, 10.34 mmol) was agitated at 60° C. for 6 hours. The reaction mixture was quenched with 150 mL of water, and extracted with 50 mL of dichloromethane three times. Combined organic layers were washed with a 1N hydrochloric acid aqueous solution, water and saturated brine, and then dried over magnesium sulfate, and a solvent was distilled off by an evaporator. The residue was washed with toluene, and thus 2-ethoxy-1,8-difluorophenanthrene-9,10-dione (86) (7.0 g, yield 70.5%) was obtained.

Workup

  1. customThe reaction mixture was quenched with 150 mL of water
  2. extractionextracted with 50 mL of dichloromethane three times
  3. washCombined organic layers were washed with a 1N hydrochloric acid aqueous solution, water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. distillationa solvent was distilled off by an evaporator
  6. washThe residue was washed with toluene

Sources & evidence

ORD record
ord-a9cec49170ea4e0cbe13c6a285cc314a
Source dataset
uspto-grants-2015_11
Patent number
US09193908B2

Reaction notes

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