Toluene → 1-ethynyl-4-fluoronaphthalene

HRID 1095216Notes

Reaction equation

HRID 1095216 reaction equation
C[C:2]1[C:3](C)=[C:4]([C:13]#[C:14]CO)[C:5]2[C:10]([C:11]=1[F:12])=[CH:9][CH:8]=[CH:7][CH:6]=2.[OH-].[Na+].C1(C)C=CC=CC=1>C(OCC)C>[F:12][C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:13]#[CH:14])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 66784011HCID 66784011, compound

Product 1

HCID 509988061-ethynyl-4-fluoronaphthaleneYield 67.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
120 °C

Procedure

Dimethylhydroxymethyl-4-fluoro-1-naphthylacetylene (1.88 g, 8.23 mmol) and NaOH (396 mg, KISHIDA CHEMICAL CO., Ltd., 0.7 mm granular, 98% article, 9.90 mmol) were placed in a 30 mL two-neck flask equipped with a reflux condenser and the air inside the flask was replaced with Ar. 20 mL of toluene was added thereto and the mixture was refluxed at 120° C. for 30 minutes. Diethyl ether was added to the reaction mixture and the mixture was washed with a saturated aqueous ammonium chloride solution and dried over magnesium sulfate. The solvent was distilled off under reduced pressure by an evaporator. The crude reaction product was purified by column chromatography (Hexane/AcOEt=100/0→1/10) using silica gel to give 946 mg of the desired compound as a yellow solid (yield: 67.5%).

Workup

  1. customequipped with a reflux condenser
  2. washthe mixture was washed with a saturated aqueous ammonium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure by an evaporator
  5. customThe crude reaction product
  6. customwas purified by column chromatography (Hexane/AcOEt=100/0→1/10)

Sources & evidence

ORD record
ord-a30bd1df33eb4cc8990a748a56ede553
Source dataset
uspto-grants-2012_03
Patent number
US08137821B2

Reaction notes

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