Triethylamine → HCID 11288995, compound

HRID 733621Notes

Reaction equation

HRID 733621 reaction equation
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:10])[CH:3]=1.[CH2:11]([C:15]1[CH:20]=[CH:19][C:18]([C:21]#[CH:22])=[CH:17][CH:16]=1)[CH2:12][CH2:13][CH3:14].CCN(CC)CC>C1COCC1.[Cu]I.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:11]([C:15]1[CH:16]=[CH:17][C:18]([C:21]#[C:22][C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:10])[CH:3]=2)=[CH:19][CH:20]=1)[CH2:12][CH2:13][CH3:14]

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 27751321-Butyl-4-ethynylbenzene

Product 1

HCID 11288995HCID 11288995, compoundYield 40%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-2-fluoro-benzaldehyde (10.0 g, 49.3 mmol), 1-butyl-4-ethynyl-benzene (8.57 g, 54.2 mmol), CuI (94 mg, 0.49 mmol) and of Et3N (9.9 g) in anhydrous THF (120 mL) were added PPh3 (258 mg, 1 mmol) and Pd(OAc)2 (221 mg). The reaction mixture was heated under argon for 3 hours. After cooling to rt, the salts were filtered off, then charcoal and silica gel were added to the solution. After filtration, the solution was concentrated under reduced pressure and the residual oil was dissolved in petroleum ether (100 mL) and stored in the freezer. The solids were filtered off and washed with cold petroleum ether to give the title compound as a white powder (5.53 g, 40%). 1H NMR (CDCl3) δ 10.33 (s, 1H), 7.82 (t, J=7.7 Hz, 1H), 7.45 (d, J=7.9 Hz, 2H), 7.38 (d, J=8.3 Hz, 1H), 7.30 (d, J=10.9 Hz, 1H), 7.18 (d, J=8.3 Hz, 2H), 2.62 (t, J=7.7 Hz, 2H), 1.58 (m, 2H), 1.36 (m, 2H), 0.92 (t, J=7.3 Hz, 3H). HPLC, Rt: 5.26 min (purity: 99.4%).

Workup

  1. temperatureThe reaction mixture was heated under argon for 3 hours
  2. filtrationthe salts were filtered off
  3. additioncharcoal and silica gel were added to the solution
  4. filtrationAfter filtration
  5. concentrationthe solution was concentrated under reduced pressure
  6. dissolutionthe residual oil was dissolved in petroleum ether (100 mL)
  7. filtrationThe solids were filtered off
  8. washwashed with cold petroleum ether

Sources & evidence

ORD record
ord-098bd7c4838248979652046f9102cef1
Source dataset
uspto-grants-2009_09
Patent number
US07589232B2

Reaction notes

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