1-(Difluoromethoxy)-4-ethynylbenzene → HCID 59305291, compound

HRID 2240932Notes

Reaction equation

HRID 2240932 reaction equation
[F:1][CH:2]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9](I)[CH:8]=1)[CH2:3][CH2:4][CH:5]=[CH2:6].[F:14][CH:15]([F:25])[O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]#[CH:24])=[CH:19][CH:18]=1>CN(C=O)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)I>[F:14][CH:15]([F:25])[O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]#[C:24][C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([CH:2]([F:1])[CH2:3][CH2:4][CH:5]=[CH2:6])[CH:8]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 2

HCID 27784971-(Difluoromethoxy)-4-ethynylbenzeneHCID 59305303HCID 59305303, compound

Product 1

HCID 59305291HCID 59305291, compoundYield 54%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 1-(1-Fluoro-pent-4-enyl)-3-iodo-benzene (0.4 g, 1.38 mmol) in DMF (6 ml) were added TEA (0.96 ml, 6.9 mmol) and 1-Difluoromethoxy-4-ethynyl-benzene (0.233 g, 1.378 mmol). The reaction was degassed by bubbling argon through it for 5 minute and then dichlorbis(triphenylphospine)palladium (0.048 g, 0.069 mmol), and copper iodide (0.013 g, 0.693 mmol) were added simultaneously. The reaction mixture was heated at 65° C. for 15 min. cooled and quenched with 0.1 N HCl (15 ml). The aqueous was extracted with Et2O (3×15 ml). The combined organic extracts were washed with brine (20 ml), dried (MgSO4), and concentrated. The crude material was purified by chromatography (2.5%-5% Ethyl acetate/Petroleum Ether) to afford the titled compound (0.246 g, 54%) as a slight orange oil, identified by NMR and mass spectral analyses; MS (EI+): 330 (M+)

Workup

  1. customThe reaction was degassed
  2. customby bubbling argon through it for 5 minute
  3. temperaturecooled
  4. customquenched with 0.1 N HCl (15 ml)
  5. extractionThe aqueous was extracted with Et2O (3×15 ml)
  6. washThe combined organic extracts were washed with brine (20 ml)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe crude material was purified by chromatography (2.5%-5% Ethyl acetate/Petroleum Ether)

Sources & evidence

ORD record
ord-fd715e086dff450b9bafcab133f12415
Source dataset
uspto-grants-2010_05
Patent number
US07723368B2

Reaction notes

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