Water → 7-bromo-2-[(E)-2-(2-chlorophenyl)ethenyl]-5-methoxy-1-benzofuran

HRID 11151Notes

Reaction equation

HRID 11151 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4]P(=O)(OCC)OCC.[Br:17][C:18]1[C:26]2[O:25][C:24]([CH:27]=O)=[CH:23][C:22]=2[CH:21]=[C:20]([O:29][CH3:30])[CH:19]=1.[H-].[Na+].O>O1CCCC1>[Br:17][C:18]1[C:26]2[O:25][C:24](/[CH:27]=[CH:4]/[C:3]3[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=3[Cl:1])=[CH:23][C:22]=2[CH:21]=[C:20]([O:29][CH3:30])[CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 12520073Diethyl ((2-chlorophenyl)methyl)phosphonateHCID 21980485HCID 21980485, compound

Product 1

HCID 219803277-bromo-2-[(E)-2-(2-chlorophenyl)ethenyl]-5-methoxy-1-benzofuranYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of diethyl 2-chlorobenzylphosphonate (4.91 g, 0.018 mol) and 7-bromo-5-methoxybenzofuran-2-carbaldehyde (11.27 g, 0.016 mol) in tetrahydrofuran (80 mL) was added sodium hydride (60% dispersion in mineral oil, 0.74 g, 0.0185 mol). After 5 min. the reaction mixture was warmed to 60° C. for 1 h. The reaction mixture was cooled to room temperature, water (10 mL) was carefully added and the tetrahydrofuran was removed. Water (50 mL) was added and the mixture was extracted with ethyl acetate (3×100 mL). The combined ethyl acetate extracts were washed with brine (50 mL), dried over magnesium sulphate, filtered and concentrated to dryness. Trituration with diethyl ether (20 mL) gave solid material which was further washed with diethyl ether (20 ml). The liquors were concentrated and triturated with diethyl ether (10 mL), the solid being collected. The combined solids gave (859) (4.89 g, 84%). 1H NMR δ (CDCl3) 7.70 (d, J=16 Hz, 1H), 7.65 (dd, J=7.7, 1.5 Hz, 1H), 7.4 (dd, J=6.0, 1 Hz, 1H), 7.23 (m, 2H), 7.05 (d, J=2.3 Hz, 1H), 6.94 (d, J=16 Hz, 1H), 6.92 (d, J=2.3 Hz, 1H), 6.72 (s, 1H), 3.82 (s, 3H); MH+:364.9, 362.9 MH−:362.9, 360.9.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe tetrahydrofuran was removed
  3. additionWater (50 mL) was added
  4. extractionthe mixture was extracted with ethyl acetate (3×100 mL)
  5. washThe combined ethyl acetate extracts were washed with brine (50 mL)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customTrituration with diethyl ether (20 mL) gave solid material which
  10. washwas further washed with diethyl ether (20 ml)
  11. concentrationThe liquors were concentrated
  12. customtriturated with diethyl ether (10 mL)
  13. customthe solid being collected

Sources & evidence

ORD record
ord-5d80c8c706d54d52b27d08212a2f23ba
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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