HCID 71145171, compound → HCID 71145601, compound

HRID 535335Notes

Reaction equation

HRID 535335 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]23[CH2:17][CH2:16][CH:13]([CH2:14][CH2:15]2)[O:12][CH2:11]3)[OH:9])=[CH:4][CH:3]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]23[CH2:15][CH2:14][CH:13]([CH2:16][CH2:17]2)[O:12][CH2:11]3)=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 71145171HCID 71145171, compound

Product 1

HCID 71145601HCID 71145601, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-Bromo-phenyl)-(2-oxa-bicyclo[2.2.2]oct-4-yl)methanol (224 mg, 0.821 mmol) in DCM (13 ml) was added a total of manganese dioxide (1.414 g, 16.264 mmol) at RT and the reaction mixture was stirred for 20 hrs. The suspension was filtered through a pad of hyflo and the residue was washed with DCM, dried in vacuo to yield the title intermediate (220 mg, 0.745 mmol, 91%) as a colourless solid.

Workup

  1. filtrationThe suspension was filtered through a pad of hyflo
  2. washthe residue was washed with DCM
  3. customdried in vacuo

Sources & evidence

ORD record
ord-65511e8424cb45b5ba5b370fd74c74fb
Source dataset
uspto-grants-2014_10
Patent number
US08859535B2

Reaction notes

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