1,4-Dibromo-2,3-butanediol → HCID 86752373, compound

HRID 481279

Reaction equation

HRID 481279 reaction equation
Br[CH2:2][CH:3]([OH:8])[CH:4]([OH:7])[CH2:5]Br.[OH2:9].[OH2:10].O.O.O.O.O.O.O.O.O.O.[P:21]([O-:25])([O-:24])([O-:23])=[S:22].[Na+].[Na+].[Na+]>CN(C=O)C.O.[N+]([O-])([O-])=O.[Ag+]>[OH2:7].[OH2:23].[OH2:9].[OH2:7].[P:21](=[S:22])([OH:25])([OH:24])[OH:23].[P:21](=[S:22])([OH:25])([OH:24])[OH:23].[CH2:2]([OH:10])[C@H:3]([C@@H:4]([CH2:5][OH:9])[OH:7])[OH:8]

Participants

6

Reactant 2

HCID 985121,4-Dibromo-2,3-butanediolHCID 45052183Sodium phosphorothioate hydrate (3:1:12)

Product 1

HCID 86752373HCID 86752373, compoundYield 285%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 1,4-dibromo-2,3-butanediol (1.0 g, 4.0 mmol) in 5 ml DMF is added to sodium thiophosphate dodecahydrate (3.8 gm, 10.1 mmol) in 20 ml H2O. The mixture is stirred overnight at room temperature. A 5% silver nitrate solution is added to precipitate excess sodium thiophosphate. The precipitate is filtered out and the filtrate dried under high vacuum. The solid residue is triturated with methanol and filtered to yield 1.8 g (3.8 mmol) of threitol bis-phosphorothioate tetrahydrate.

Workup

  1. customto precipitate excess sodium thiophosphate
  2. filtrationThe precipitate is filtered out
  3. customthe filtrate dried under high vacuum
  4. customThe solid residue is triturated with methanol
  5. filtrationfiltered

Sources & evidence

ORD record
ord-4dd8f3956e434e258e1ccf9a607920c0
Source dataset
uspto-grants-1998_08
Patent number
US05789219

Linked notes

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