Boron tribromide → HCID 53663674, compound

HRID 1824903Notes

Reaction equation

HRID 1824903 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 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-03f0fb48af4c4beaa122966b0dbb1f1b
Source dataset
uspto-grants-2006_05
Patent number
US07045540B2

Reaction notes

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