1,3-Dibromo-5,5-dimethylhydantoin → 4-Bromomethylphenyl 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranoside

HRID 863786Notes

Reaction equation

HRID 863786 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@@H:17]([O:23][C:24](=[O:26])[CH3:25])[C@@H:16]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[O:15][C@@H:6]1[O:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=1)(=[O:3])[CH3:2].[Br:32]N1C(C)(C)C(=O)N(Br)[C:34]1=[O:35]>>[C:1]([O:4][C@@H:5]1[C@@H:18]([O:19][C:20](=[O:22])[CH3:21])[C@@H:17]([O:23][C:24](=[O:26])[CH3:25])[C@@H:16]([CH2:27][O:28][C:29](=[O:31])[CH3:30])[O:15][C@@H:6]1[O:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][Br:32])=[CH:12][CH:13]=1)(=[O:3])[CH3:2].[CH3:34][OH:35]

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 541416384-Methylphenyl 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranoside

Product 2

HCID 887MethanolYield 76%HCID 539280404-Bromomethylphenyl 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosideYield 422.9%

Procedure

1.4 g (3.2 mmoles) of 4-methylphenyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside (71) and 0.46 g (1.6 mmole) of 1,3-dibromo 5,5-dimethylhydantoine are added in 100 ml of carbone tetrachloride, and the mixture est refluxed under irradiation with light (1 000 W) for 15 minutes. After cooling, the reaction medium is filtered and the filtrate is then evaporated to dryness. 3.5 g of 4-bromomethylphenyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside (72) are isolated by crystallization from methanol (yield=76%).

Workup

  1. temperaturethe mixture est refluxed under irradiation with light (1 000 W) for 15 minutes
  2. temperatureAfter cooling
  3. filtrationthe reaction medium is filtered
  4. customthe filtrate is then evaporated to dryness

Sources & evidence

ORD record
ord-084f5d8f190e4bb0a3d0ddded00d656d
Source dataset
uspto-grants-1996_10
Patent number
US05561119

Reaction notes

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