Water → HCID 2306330, compound

HRID 1861946Notes

Reaction equation

HRID 1861946 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23].B(Br)(Br)Br.O>C(Cl)Cl>[OH:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[CH2:12][N:13]1[C:17](=[O:18])[C:16]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:15]2[C:14]1=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 18621716HCID 18621716, compound

Product 1

HCID 2306330HCID 2306330, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of the compound (937 mg) obtained in Example 117 in anhydrous methylene chloride (30 ml), a solution of boron tribromide in methylene chloride (1.0 M, 9 ml) was added dropwise at −78° C. in a nitrogen atmosphere and the mixture was stirred at −78° C. for 1 h, then stirred at room temperature for 21 h. Water was added to the reaction mixture, which was extracted with chloroform. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=1:1) to give 743 mg of the titled compound (yield, 83%).

Workup

  1. stirringstirred at room temperature for 21 h
  2. extractionwas extracted with chloroform
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-b1d75909e51e48fabaf0cd7b09a6625b
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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