Boron tribromide → HCID 53663674, compound

HRID 2253486Notes

Reaction equation

HRID 2253486 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[CH:20][C:21]([OH:23])=[O:22])=[CH:15][CH:14]=1)[CH:8]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:7][CH2:6]2.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[CH:20][C:21]([OH:23])=[O:22])=[CH:15][CH:14]=1)[CH:8]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 54486062HCID 54486062, compound

Product 1

HCID 53663674HCID 53663674, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of ether 6e (120 mg, 0.312 mmol) in CH2Cl2 (12 mL) at 0° C. was added 1M boron tribromide in CH2Cl2 (4 mL). The mixture was stirred for 1.5 h at room temperature and then quenched with ice/H2O. After stirring for 2 h, the mixture was extracted with CH2Cl2. The combined organic layers were washed with water and dried (MgSO4). The solvent was removed under reduced pressure and the residue chromatographed (silica gel, 10-20% methanol/CH2Cl2)to give phenol 6f as a white solid (45 mg, 39%): ESI m/z: 369 (M−H−, 100%).

Workup

  1. customquenched with ice/H2O
  2. stirringAfter stirring for 2 h
  3. extractionthe mixture was extracted with CH2Cl2
  4. washThe combined organic layers were washed with water
  5. dry with materialdried (MgSO4)
  6. customThe solvent was removed under reduced pressure
  7. customthe residue chromatographed (silica gel, 10-20% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-99093a504e7c491aab9ed762cfc240c8
Source dataset
uspto-grants-2008_01
Patent number
US07323587B2

Reaction notes

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