Boron tribromide → HCID 22459006, compound

HRID 613418Notes

Reaction equation

HRID 613418 reaction equation
[CH3:1][C:2]([CH3:16])([CH3:15])[CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][C:11]([O:13]C)=[CH:12][C:7]=2[O:6][CH:5]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:1][C:2]([CH3:16])([CH3:15])[CH2:3][C:4]1[C:8]2[CH:9]=[CH:10][C:11]([OH:13])=[CH:12][C:7]=2[O:6][CH:5]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 22459083HCID 22459083, compound

Product 1

HCID 22459006HCID 22459006, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a -10° C. solution of the product of Step D (2.379 grams) in dry methylene chloride (35 mL) was added 1M boron tribromide solution (CH2Cl2 ; 3.70 mL). Warming to ambient temperature was followed by stirring for 1 hour. The reaction was partitioned between isopropyl acetate and aqueous sodium bicarbonate. The organic was washed twice with water and dried over magnesium sulfate. Filtration and removal of volatiles provided a residue which was chromatographed over silica gel (5:1 hex/ethyl acetate), giving the title compound.

Workup

  1. customThe reaction was partitioned between isopropyl acetate and aqueous sodium bicarbonate
  2. washThe organic was washed twice with water
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and removal of volatiles
  5. customprovided a residue which
  6. customwas chromatographed over silica gel (5:1 hex/ethyl acetate)

Sources & evidence

ORD record
ord-9877585bb1714a5d8c22249daf29739e
Source dataset
uspto-grants-1999_12
Patent number
US06008237

Reaction notes

Loading…