Hydrogen Bromide → HCID 12905063, compound

HRID 2228430Notes

Reaction equation

HRID 2228430 reaction equation
C(O[CH:5]1[O:34][C@H:33]([CH2:35][O:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@H:24]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:6]1[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.[BrH:44].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(OC(C)C)(C)C>[CH2:8]([O:7][C@@H:6]1[C@@H:15]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@@H:24]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C@@H:33]([CH2:35][O:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[O:34][C@@H:5]1[Br:44])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 260Hydrogen Bromide2×HCID 516892Sodium BicarbonateHCID 1130776780300-97-6

Product 1

HCID 12905063HCID 12905063, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7914Diisopropyl EtherSolvent2×

Conditions

Temperature
-5 °C

Procedure

2,3,4,6 -tetra-O-benzyl-D-galactopyranosyl acetate (79.8 g) was dissolved in the mixed solvent of toluene (160 ml) and isopropyl ether (520 ml), and cooled to a temperature in the range of −10-0° C. An isopropyl ether solution containing 2.0 equivalents of HBr (2.8 mmole/ml, ca. 100 ml) was added to this mixture. After stirring at −10-0° C. for about 90 minutes, unreacted HBr in the reaction mixture was neutralized with 5% aqueous sodium hydrogen carbonate solution. The total volume of the mixture was separated in a separatory funnel, the aqueous layer was discarded, and the organic layer was washed twice with 10% aqueous sodium chloride solution, and concentrated under reduced pressure to give 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl bromide (GalBr) in the form of syrup.

Workup

  1. additionwas added to this mixture
  2. customThe total volume of the mixture was separated in a separatory funnel
  3. washthe organic layer was washed twice with 10% aqueous sodium chloride solution
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e554337d2ab149a3b24606d051c5a4a8
Source dataset
uspto-grants-2002_07
Patent number
US06417167B1

Reaction notes

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