4-Bromostyrene → 1-(4-bromophenyl)ethane-1,2-diol

HRID 2364632Notes

Reaction equation

HRID 2364632 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5](C=C)=[CH:4][CH:3]=1.C[N+]1([O-])[CH2:16][CH2:15][O:14]CC1.CC(C)=[O:20].O>CCOC(C)=O.[Os](=O)(=O)(=O)=O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:15]([OH:14])[CH2:16][OH:20])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 162634-BromostyreneHCID 82029Methyl morpholine oxideHCID 18366337Propan-2-one--water (1/1)

Product 1

HCID 111486511-(4-bromophenyl)ethane-1,2-diolYield 28%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-Bromostyrene (1.00 g, 5.46 mmol) was dissolved in 25 mls of 2:1 water acetone. To this was added 4-methylmorpholine N-oxide (0.704 g, 6.01 mmole) and osmium tetroxide (0.167 g, 0.061 mmole, 2.5% in t-BuOH). This mixture was stirred at room temperature for 16 hours, then diluted with EtOAc, washed once with 1N aq. HCl, once with saturated sodium bicarbonate solution, dried over sodium sulfate and concentrated under reduced pressure. The resulting crude product was purified by Flash 40 Biotage (40M cartridge, 100% EtOAc as the eluant) to give 335 mgs (28%) of 1-(4-bromophenyl)ethane-1,2-diol as a white solid.

Workup

  1. washwashed once with 1N aq. HCl, once with saturated sodium bicarbonate solution
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting crude product was purified by Flash 40 Biotage (40M cartridge, 100% EtOAc as the eluant)

Sources & evidence

ORD record
ord-fa57964f79c6470c90e6d181f478b366
Source dataset
uspto-grants-2014_04
Patent number
US08691809B2

Reaction notes

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