Boron tribromide → HCID 22459036, compound

HRID 613422Notes

Reaction equation

HRID 613422 reaction equation
B(Br)(Br)Br.[C:5]1([CH2:11][CH2:12][C:13]2[C:17]3[CH:18]=[CH:19][C:20]([O:22]C)=[CH:21][C:16]=3[O:15][CH:14]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>>[C:5]1([CH2:11][CH2:12][C:13]2[C:17]3[CH:18]=[CH:19][C:20]([OH:22])=[CH:21][C:16]=3[O:15][CH:14]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 25134Boron tribromideHCID 22459084HCID 22459084, compound

Product 1

HCID 22459036HCID 22459036, compound

Procedure

A stirred, -10° C. solution of the product from Step B (2.066 grams; dry methylene chloride; 20 mL) was treated with 1M boron tribromide solution (methylene chloride; 8.40 mL). After 15 minutes, the reaction was warmed to ambient temperature and stirred another 15 minutes. It was partitioned between isopropyl acetate and pH7 phosphate buffer, then washed twice more with pH7 buffer and dried over magnesium sulfate. Filtration and evaporation produced an oil which was chromatographed over silica gel (step gradient; CH2Cl2 to 40:1 CH2Cl2 /ethyl acetate). The title compound was isolated as a pale yellow solid.

Workup

  1. customIt was partitioned between isopropyl acetate and pH7 phosphate buffer
  2. washwashed twice more with pH7 buffer
  3. dry with materialdried over magnesium sulfate
  4. filtrationFiltration and evaporation
  5. customproduced an oil which
  6. customwas chromatographed over silica gel (step gradient; CH2Cl2 to 40:1 CH2Cl2 /ethyl acetate)

Sources & evidence

ORD record
ord-41397c22d8b149ae8d345bc5aaf55a6d
Source dataset
uspto-grants-1999_12
Patent number
US06008237

Reaction notes

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