Triethylamine → 4-Fluoro-4'-(phenylethynyl)benzophenone

HRID 1158548Notes

Reaction equation

HRID 1158548 reaction equation
Br[C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)=[O:7])=[CH:4][CH:3]=1.[C:17]1([C:23]#[CH:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I.C1(C)C=CC=CC=1>[F:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]([C:5]2[CH:15]=[CH:16][C:2]([C:24]#[C:23][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:3][CH:4]=2)=[O:7])=[CH:9][CH:10]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 74951(4-Bromophenyl)(4-fluorophenyl)methanone

Product 1

HCID 40956574-Fluoro-4'-(phenylethynyl)benzophenone

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

In an inert atmosphere glovebox, 4-bromo-4′-fluorobenzophenone (10 g, 35.8 mmol), PdCl2(PPh3)2 (250 mg), CuI (680 mg), phenylacetylene (4.02 g, 1.1 eq), triethylamine (3.6 g, 1 eq), and toluene (25 mL) were combined. The flask was closed and heated to 70° C. for 24 h. The mixture was poured over ice and extracted with methylene chloride, which was separated and evaporated. The residue was recrystallized twice from hot ethanol using decolorizing charcoal to give the title product as white crystals.

Workup

  1. customThe flask was closed
  2. additionThe mixture was poured over ice
  3. extractionextracted with methylene chloride, which
  4. customwas separated
  5. customevaporated
  6. customThe residue was recrystallized twice from hot ethanol using

Sources & evidence

ORD record
ord-f11959b502fd4079acf7c935cb3587f0
Source dataset
uspto-grants-2010_10
Patent number
US07811499B2

Reaction notes

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