Boron tribromide → HCID 135532374, compound

HRID 1977427Notes

Reaction equation

HRID 1977427 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[CH:12]=[N:11][CH:10]=[C:9]3[S:13][C:14]([C:16]4[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=4)=[CH:15][C:8]=23)=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][C:7]2[CH:12]=[N:11][CH:10]=[C:9]3[S:13][C:14]([C:16]4[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=4)=[CH:15][C:8]=23)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21997824HCID 21997824, compound

Product 1

HCID 135532374HCID 135532374, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Example 270B (0.09 g, 0.24 mmmol) in anhydrous CH2Cl2 (4 mL) was added a 1 M solution of boron tribromide in CH2Cl2 (0.96 mL, 0.96 mmol). After 2 hours, the reaction was quenched by slow addition of MeOH (2 mL) and then concentrated. The residue was diluted with CH2Cl2 (50 mL) and organic washed with 1:1 sat. NaHCO3/brine (50 mL), partially dried (Na2SO4), then concentrated. The residue was purified by flash chromatography on silica gel using EtOAc/hexane as eluent to yield the title compound as a solid (0.08, 96%).

Workup

  1. customthe reaction was quenched by slow addition of MeOH (2 mL)
  2. concentrationconcentrated
  3. additionThe residue was diluted with CH2Cl2 (50 mL)
  4. washorganic washed with 1:1 sat. NaHCO3/brine (50 mL)
  5. dry with materialpartially dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-39599b244513491b8ca432ac7fc3aabb
Source dataset
uspto-grants-2001_05
Patent number
US06232320B1

Reaction notes

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