Hydrogen Bromide → HCID 12094545, compound

HRID 2120157Notes

Reaction equation

HRID 2120157 reaction equation
Br.C[O:3][C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[CH:12][C:13]3[C:17]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)=[CH:16][O:15][C:14]=3[CH:24]=2)[CH:7]=[CH:8][CH:9]=1.[OH-].[Na+]>>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:17]2[C:13]3[CH:12]=[CH:11][C:10]([C:6]4[CH:5]=[C:4]([OH:3])[CH:9]=[CH:8][CH:7]=4)=[CH:24][C:14]=3[O:15][CH:16]=2)[CH:19]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 12094543HCID 12094543, compound

Product 1

HCID 12094545HCID 12094545, compoundYield 76%

Procedure

47% hydrobromic acid solution (1.6 ml) was added to 3-[6-(3-methoxyphenyl)benzo[b]furan-3-yl]pyridine (80 mg, 0.2655 mmol) obtained in Example 5, and the mixture was refluxed for 24 hours. After neutralizing with 2N sodium hydroxide aqueous solution and a saturated aqueous solution of sodium bicarbonate, and extracting with ethyl acetate, the organic layer was washed with water, then with saturated brine, and dried with anhydrous magnesium sulfate, followed by evaporating the solvent under reduced pressure. The product was crystallized in ether-chloroform to obtain a white powder of 3-[3-(3-pyridyl)benzo [b]furan-6-yl]phenol (58 mg, 76%).

Workup

  1. temperaturethe mixture was refluxed for 24 hours
  2. extractiona saturated aqueous solution of sodium bicarbonate, and extracting with ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materialwith saturated brine, and dried with anhydrous magnesium sulfate
  5. customby evaporating the solvent under reduced pressure
  6. customThe product was crystallized in ether-chloroform

Sources & evidence

ORD record
ord-3b14550717814c6f99fe56aedf6dfa8f
Source dataset
uspto-grants-2004_02
Patent number
US06689798B2

Reaction notes

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