Triethylamine → 4-Fluoro-2-(4-methanesulfonyl-phenylethynyl)-benzaldehyde

HRID 1644720Notes

Reaction equation

HRID 1644720 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH3:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[CH:2].C(N(CC)CC)C.Br[C:21]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:22]=1[CH:23]=[O:24]>ClCCl.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>[F:29][C:27]1[CH:28]=[CH:21][C:22]([CH:23]=[O:24])=[C:25]([C:2]#[C:1][C:3]2[CH:4]=[CH:5][C:6]([S:9]([CH3:12])(=[O:10])=[O:11])=[CH:7][CH:8]=2)[CH:26]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27733192-Bromo-4-fluorobenzaldehydeHCID 220426121-Ethynyl-4-(methanesulfonyl)benzene

Product 1

HCID 593508304-Fluoro-2-(4-methanesulfonyl-phenylethynyl)-benzaldehydeYield 79.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A degassed mixture of 1-ethynyl-4-methanesulfonyl-benzene (2.5 g, 13.87 mmol), bis(triphenylphosphine)palladium(II) chloride (0.49 g, 0.69 mmol), copper(I) iodide (0.13 g, 0.69 mmol), triethylamine (28 mL), and 2-bromo-4-fluorobenzaldehyde (3.38 g, 16 mmol) in dichloromethane (10 mL) was stirred at 80° C. for 3.5 hours, then at room temperature overnight. The reaction mixture was partitioned between dichloromethane and water. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (RediSep® Flash column, 230-400 mesh, 15-35% ethyl acetate in hexane) gave 4-fluoro-2-(4-methanesulfonyl-phenylethynyl)-benzaldehyde (3.32 g, 79%). MS (ESI+) cald. for C16H11FO3S [(M+H)+] 302, obsd. 302.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe reaction mixture was partitioned between dichloromethane and water
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5476d957c5804cba8b67c683dddda991
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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