Bromine → HCID 22020923, compound

HRID 1793324Notes

Reaction equation

HRID 1793324 reaction equation
[Br:1]Br.[O:3]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[O:6][CH:5]([CH2:13][OH:14])[CH2:4]1>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+].[O-]S([O-])=O.[Na+].[Na+]>[Br:1][C:10]1[CH:11]=[C:12]2[O:3][CH2:4][CH:5]([CH2:13][OH:14])[O:6][C:7]2=[N:8][CH:9]=1

Participants

6

Reactant 2

HCID 24408Bromine2×HCID 22020920152895-57-3

Product 1

HCID 22020923HCID 22020923, compoundYield 40.6%

Reagents, catalysts & solvents 3

HCID 24437Sodium SulfiteCatalystHCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

Bromine (0.009 mol) was added dropwise to a solution of 2,3-dihydro-1,4-dioxino[2,3-b]pyridine-3-methanol (0.009 mol) in DCM (100 ml) and Na2CO3 saturated solution (50 ml), stirred at room temperature. The reaction mixture was stirred for 16 hours at room temperature. More bromine (0.009 mol) was added and the reaction mixture was stirred for 3 more days at room temperature. A few drops of Na2SO3 were added and the mixture was stirred for 15 minutes. The separated organic layer was dried, filtered and the solvent evaporated. The residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2/CH3OH 100/0; 98/2). The desired fractions were collected and the solvent was evaporated, yielding 0.9 g of 7-bromo-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine-3-methanol (intermediate 35).

Workup

  1. stirringThe reaction mixture was stirred for 16 hours at room temperature
  2. stirringthe reaction mixture was stirred for 3 more days at room temperature
  3. stirringthe mixture was stirred for 15 minutes
  4. customThe separated organic layer was dried
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe residue was purified by short open column chromatography over silica gel (eluent: CH2Cl2/CH3OH 100/0; 98/2)
  8. customThe desired fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7c434df8182b48b2920976e739a5bf0b
Source dataset
uspto-grants-2006_07
Patent number
US07081453B2

Reaction notes

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