m-Chloroperbenzoic acid → 1,5:2,3-Dianhydro-3-C-(3-bromophenyl)-4-deoxypentitol

HRID 1842266Notes

Reaction equation

HRID 1842266 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[CH:14]=[C:15]([C:19]2[CH2:20][CH2:21][O:22][CH2:23][CH:24]=2)[CH:16]=[CH:17][CH:18]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Br:12][C:13]1[CH:14]=[C:15]([C:19]23[O:9][CH:20]2[CH2:21][O:22][CH2:23][CH2:24]3)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 57475766HCID 57475766, compound

Product 1

HCID 578277501,5:2,3-Dianhydro-3-C-(3-bromophenyl)-4-deoxypentitolYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperbenzoic acid (purity: 80%, 25.1 g) was added to a solution of 4-(3-bromophenyl)-3,6-dihydro-2H-pyran (21.4 g) in dichloromethane (400 mL) in an ice bath. The mixture was stirred at the same temperature for three hours, and then warmed to room temperature and stirred for five hours. Ice and a saturated sodium bicarbonate solution were added to the reaction mixture, and the organic layer was separated. The organic layer was sequentially washed with a saturated sodium bicarbonate solution, a sodium thiosulfate solution and brine. The aqueous layers were combined and extracted with ethyl acetate, and the organic layer was sequentially washed with a sodium bicarbonate solution, a sodium thiosulfate solution and brine. The organic layers were combined and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (17.5 g).

Workup

  1. stirringstirred for five hours
  2. customthe organic layer was separated
  3. washThe organic layer was sequentially washed with a saturated sodium bicarbonate solution
  4. extractionextracted with ethyl acetate
  5. washthe organic layer was sequentially washed with a sodium bicarbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2289803756c843d488c03d2ca13eef98
Source dataset
uspto-grants-2015_02
Patent number
US08946210B2

Reaction notes

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