Hydrogen Bromide → Bromide ion

HRID 2369179Notes

Reaction equation

HRID 2369179 reaction equation
[C:1]([O:4][C@H:5]([C@H:8]([C@@H:13]([C@@H:18]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:19][C:20](=[O:22])[CH3:21])[O:14][C:15](=[O:17])[CH3:16])[O:9][C:10](=[O:12])[CH3:11])[CH:6]=[O:7])(=[O:3])[CH3:2].C(Cl)Cl.[BrH:31]>CC(O)=O>[C:1]([O:4][C@H:5]([C@H:8]([C@@H:13]([C@@H:18]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:19][C:20](=[O:22])[CH3:21])[O:14][C:15](=[O:17])[CH3:16])[O:9][C:10](=[O:12])[CH3:11])[CH:6]=[O:7])(=[O:3])[CH3:2].[Br-:31]

Participants

6

Reactant 3

HCID 260Hydrogen Bromide2×HCID 6344Dichloromethane2×HCID 92972D-Glucose, 2,3,4,5,6-pentaacetate

Product 2

HCID 259Bromide ionHCID 92972D-Glucose, 2,3,4,5,6-pentaacetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 500 ml flask was added 50 g of glucose pentaacetate (C6H22O11) and 80 ml of methylene chloride. The mixture was stirred at ice-water bath for 20 min HBr in HOAc (33%, 50 ml) was added to the reaction mixture. After stirring for 2.5 hr another 5 ml of HBr was added to the mixture. After another 30 min, the mixture was added 600 ml of methylene chloride. The organic mixture was washed with cold water (200 ml×2), Saturated NaHCO3 (200 ml×2), water (200 ml) and brine (200 ml×2). The organic layer was dried over Na2SO4 and the mixture was evaporated at RT to give white solid as final product, bromide derivative, IntD1 (˜95% yield). C14H19BrO9, TLC Rf=0.49, SiO2, 40% ethyl acetate/60% hexanes; Exact Mass 410.02.

Workup

  1. additionwas added to the reaction mixture
  2. additionwas added to the mixture
  3. washThe organic mixture was washed with cold water (200 ml×2), Saturated NaHCO3 (200 ml×2), water (200 ml) and brine (200 ml×2)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe mixture was evaporated at RT

Sources & evidence

ORD record
ord-b0073eb6a72346479933824f89d020e8
Source dataset
uspto-grants-2014_04
Patent number
US08703923B2

Reaction notes

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