Hydrochloric Acid → HCID 21870536, compound

HRID 992188Notes

Reaction equation

HRID 992188 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([F:24])[CH:18]=3)[CH:13]=2)[CH:8]=1)(=O)=O.CN(C=O)C.[CH3:32][C:33]#[CH:34].Cl>C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu](I)I>[F:24][C:19]1[CH:18]=[C:17]([C:12]2[CH:11]=[CH:10][C:9]3[C:14](=[CH:15][CH:16]=[C:7]([C:32]#[C:33][CH3:34])[CH:8]=3)[CH:13]=2)[CH:22]=[CH:21][C:20]=1[F:23]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6335PropyneHCID 21870955HCID 21870955, compound

Product 1

HCID 21870536HCID 21870536, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

11.4 g of 6-(3,4-difluorophenyl)-2-naphthyl trifluoromethanesulfonate and 60 ml of DMF were dissolved in 20 ml of triethylamine. To the solution were then added 0.4 g of tetrakis(triphenylphosphine)palladium (0) and 0.1 g of copper iodide (I). Methyl acetylene was then introduced into the reaction mixture at ordinary temperature and pressure. The reaction mixture was then stirred for 2 hours. The reaction solution was neutralized with a 10% hydrochloric acid, extracted with 100 ml of toluene, and then washed with water and saturated brine. The solvent was then distilled off. The residue was then purified through silica gel column chromatography (hexane) to obtain 7.4 g of 2-(3,4-difluorophenyl)-6-(1-propinyl)naphthalene.

Workup

  1. extractionextracted with 100 ml of toluene
  2. washwashed with water and saturated brine
  3. distillationThe solvent was then distilled off
  4. customThe residue was then purified through silica gel column chromatography (hexane)

Sources & evidence

ORD record
ord-ba83de0ba15b421091fbe841aa72c9c3
Source dataset
uspto-grants-2002_10
Patent number
US06468607B1

Reaction notes

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