Chlorosuccinimide → Methyl 4-Bromo-5-chloro-2-furoate

HRID 1961165Notes

Reaction equation

HRID 1961165 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[O:5][CH:6]=1.C1C(=O)N([Cl:18])C(=O)C1>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:7]([O:9][CH3:10])=[O:8])[O:5][C:6]=1[Cl:18]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 12239443Methyl 4-bromofuran-2-carboxylate

Product 1

HCID 12239445Methyl 4-Bromo-5-chloro-2-furoateYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 4-bromo-2-furancarboxylate (1.4 g, 6.83 mmol) and NCS (0.912 g, 6.83 mmol) in N,N-dimethylformamide (13.7 ml) was stirred in a sealed tube for 1 h at 100° C. After 1 h, the solution was partitioned between DCM-H2O and the aqueous phase was washed several times with DCM. The combined organic fractions were dried over Na2SO4, concentrated and purified via column chromatography (2-10% EtOAc in hexanes) affording methyl 4-bromo-5-chloro-2-furancarboxylate (1.348 g, 5.12 mmol, 75% yield) as a white solid: LCMS (ES) m/e 238, 240, 242 (M, M+2, M+4)+.

Workup

  1. customthe solution was partitioned between DCM-H2O
  2. washthe aqueous phase was washed several times with DCM
  3. dry with materialThe combined organic fractions were dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified via column chromatography (2-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1311c8c689aa4358bfc8aa63ee81dce9
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

Loading…