Carbon Tetrachloride → 2-(7-Bromo-3-chloromethyl-naphthalen-1-yloxy)-5-ethanesulfonyl-pyridine

HRID 238635Notes

Reaction equation

HRID 238635 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([Cl:24])(Cl)(Cl)Cl.[Br:25][C:26]1[CH:27]=[C:28]2[C:33](=[CH:34][CH:35]=1)[CH:32]=[C:31](CO)[CH:30]=[C:29]2[O:38][C:39]1[CH:44]=[CH:43][C:42]([S:45]([CH2:48][CH3:49])(=[O:47])=[O:46])=[CH:41][N:40]=1>O1CCCC1.O>[Br:25][C:26]1[CH:27]=[C:28]2[C:33]([CH:32]=[C:31]([CH2:20][Cl:24])[CH:30]=[C:29]2[O:38][C:39]2[CH:44]=[CH:43][C:42]([S:45]([CH2:48][CH3:49])(=[O:46])=[O:47])=[CH:41][N:40]=2)=[CH:34][CH:35]=1

Participants

6

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 59326541[6-Bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalen-2-yl]-methanol

Product 1

HCID 593265982-(7-Bromo-3-chloromethyl-naphthalen-1-yloxy)-5-ethanesulfonyl-pyridineYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

After a solution of triphenylphosphine (330 mg, 1.26 mmol) and carbon tetrachloride (2 mL) in anhydrous tetrahydrofuran (6 mL) was stirred at room temperature for 10 minutes under a nitrogen atmosphere, [6-bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalen-2-yl]-methanol (265 mg, 0.63 mmol) was introduced as a solid. The resulting mixture was heated at reflux for 4 hours, cooled to room temperature, then diluted with water (10 mL), and extracted with ethyl acetate (30 mL×2). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography (silica gel, 100-200 mesh, 5% ethyl acetate in petroleum ether) to afford 2-(7-bromo-3-chloromethyl-naphthalen-1-yloxy)-5-ethanesulfonyl-pyridine (210 mg, 76%) as a yellow oil.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 4 hours
  3. extractionextracted with ethyl acetate (30 mL×2)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (silica gel, 100-200 mesh, 5% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-e41009f68fb94cdaa825796b4019db4a
Source dataset
uspto-grants-2014_02
Patent number
US08642629B2

Reaction notes

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