Dichloromethane → 2-(6-Methoxy-2-naphthyl)-1-benzofuran

HRID 1359190Notes

Reaction equation

HRID 1359190 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](Br)[CH:7]=[CH:6]2.[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH:16]=[C:15]1B(O)O.C(=O)([O-])[O-].[K+].[K+].ClCCl>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:15]1[O:14][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH:16]=1)[CH:7]=[CH:6]2

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 787862-Bromo-6-methoxynaphthaleneHCID 2776266Benzo[b]furan-2-boronic acid

Product 1

HCID 110766242-(6-Methoxy-2-naphthyl)-1-benzofuranYield 81.4%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70.5 °C

Procedure

A mixture of 6-methoxy-2-bromonaphthalene (10.1 g, 42.6 mmol), 2-benzofuranboronic acid (8.28 g, 51.1 mmol), potassium carbonate (11.7 g, 84.8 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) complex with dichloromethane (1:1) (0.887g, 1.09 mmol) in dioxane (420 mL) and water (42 mL) was heated to 69-72° C. for 2 hours. It was allowed to cool to room temperature and solvent evaporated. The residue was paroom temperatureitioned, with heating (because the product is very insoluble) in chloroform/2N hydrochloric acid. The organic phase was washed with water and brine. It was dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography using 15-75% chloroform in hexane and 100% chloroform as eluants. It was dried for 30 minutes at 60° C. to afford 2-(6-methoxy-2-naphthyl)-1-benzofuran as a light yellow-brown solid (9.51 g, 81%): mp 194-195° C.; mass spectrum (+EI, M+) m/z 274. 1HNMR (400 MHz, DMSO-d6): δ8.4 (s, 1H), 7.9-8.0 (m, 3H), 7.65-7.7 (m, 2H), 7.5 (s, 1H), 7.35 (d, 1H, J=2.5 Hz), 7.2-7.35 (m, 3H), and 3.9 ppm (s, 3H). Elemental Analysis for C19H14O2: Calculated: C, 83.19; H, 5.14; N, 0.00; Found: C, 82.96; H, 4.98; N, 0.01;

Workup

  1. temperatureto cool to room temperature
  2. customsolvent evaporated
  3. temperaturewith heating (because the product
  4. washThe organic phase was washed with water and brine
  5. dry with materialIt was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography
  9. customIt was dried for 30 minutes at 60° C.

Sources & evidence

ORD record
ord-1f26dfaa5d944d36a272fd1a656fea95
Source dataset
uspto-grants-2003_07
Patent number
US06599925B2

Reaction notes

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