Boron tribromide → HCID 178517667, compound

HRID 518476Notes

Reaction equation

HRID 518476 reaction equation
[Cl:1][C:2]1[O:12][C:5]2=[C:6]([O:10]C)[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[O:12][C:5]2=[C:6]([OH:10])[N:7]=[CH:8][CH:9]=[C:4]2[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 1180221532-Chloro-7-methoxyfuro[2,3-c]pyridine

Product 1

HCID 178517667HCID 178517667, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 0.25M solution of 2-chloro-7-methoxyfuro[2,3-c]pyridine (263 mg, 1.4 mmol) in DCM stirred at −0° C. under an atmosphere of nitrogen was treated with BBr3 (1 M in DCM, 4.3 mL, 4.3 mmol) dropwise over 5 min. The mixture was allowed to warm gradually to rt. After the mixture was allowed to stir overnight, it was poured into ice water and extracted with DCM (3×15 mL). The combined organic layers were washed with water and brine (10 mL), dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography using a gradient of EtOAc (15 to 75%) in hexanes to afford the title compound (115 mg, 47%) as light yellow solid. LCMS (M+H)+=170.

Workup

  1. extractionextracted with DCM (3×15 mL)
  2. washThe combined organic layers were washed with water and brine (10 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-60fa9eb864ed4db3b0cb25a72c3d39e1
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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