Ethanol → HCID 21844454, compound

HRID 361905Notes

Reaction equation

HRID 361905 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[C:7]([C:20]([OH:22])=[O:21])[C:6]=2[CH:23]=1.S(Cl)(Cl)=O.[CH2:28](O)[CH3:29]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][CH2:11][C:12]3[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=3)=[C:7]([C:20]([O:22][CH2:28][CH3:29])=[O:21])[C:6]=2[CH:23]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl Chloride2×HCID 21844416HCID 21844416, compound

Product 1

HCID 21844454HCID 21844454, compound

Procedure

1H-NMR (DMSO-d6) δ: 3.00 (2H, m), 3.35 (2H, m), 3.69 (3H, s), 6.80 (2H, d, J=8.0 Hz), 7.07 (2H, d, J=8.0 Hz), 7.50 (1H, dd), 7.55 (1H, d), 8.00 (1H, d) d) 64.2 g of 5-bromo-2-[2-(4-methoxyphenyl)-ethyl]-3-benzofurancarboxylic acid obtained in the above step c) was suspended in 900 ml of ethanol. 30 ml of thionyl chloride was added dropwise to the above suspension with ice cooling. After refluxing under heating for 5 hours, 50 ml of thionyl chloride was further added dropwise to the resulting reaction mixture, followed by additional refluxing under heating for 3 hours. The reaction solution thus obtained was concentrated to dryness, and the resulting residue was mixed with water to collect insoluble materials by filtration. The thus collected insoluble materials were dissolved in ethyl acetate and washed with a saturated sodium bicarbonate aqueous solution, water, a saturated sodium chloride aqueous solution in that order, followed by drying to distill off the solvent. Thereafter, the resulting residue was suspended in ethanol and then collected by filtration to obtain 59.23 g of ethyl 5-bromo-2-[2-(4-methoxyphenyl)ethyl]-3-benzofurancarboxylate.

Workup

  1. customobtained in the above step c)
  2. temperatureAfter refluxing
  3. temperatureunder heating for 5 hours
  4. temperatureby additional refluxing
  5. temperatureunder heating for 3 hours
  6. customThe reaction solution thus obtained
  7. concentrationwas concentrated to dryness
  8. additionthe resulting residue was mixed with water
  9. customto collect insoluble materials
  10. filtrationby filtration
  11. dissolutionThe thus collected insoluble materials were dissolved in ethyl acetate
  12. washwashed with a saturated sodium bicarbonate aqueous solution, water
  13. customby drying
  14. distillationto distill off the solvent
  15. filtrationcollected by filtration

Sources & evidence

ORD record
ord-57b0f7ef2a7948fab65097651bf5d53c
Source dataset
uspto-grants-1999_02
Patent number
US05866577

Reaction notes

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