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

HRID 1914846Notes

Reaction equation

HRID 1914846 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5](C=C)=[CH:4][CH:3]=1.[NH+]1([O-])[CH2:15][CH2:14][O:13]CC1.S([O-])([O-])(=[O:19])=S.[Na+].[Na+]>CC(C)=O.O.O=[Os](=O)(=O)=O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:14]([OH:13])[CH2:15][OH:19])=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 162634-BromostyreneHCID 24477Sodium ThiosulfateHCID 15900019Morpholine oxide

Product 1

HCID 111486511-(4-bromophenyl)ethane-1,2-diol

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalyst2×HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To 4-bromostyrene (Compound [LXI], 366 mg, 2 mmol, 1 eq.) in acetone (10 mL) was added morpholine N-oxide (953 mg of a 50% solution in H2O, 4.0 mmol, 2.0 eq.) and then OsO4 (1.3 g for a 4% OsO4 in H2O, 0.2 mmol, 0.1 eq). The mixture was allowed to stir at room temperature for 1 hour. The reaction mixture was then added to an aqueous solution of sodium thiosulfate and then extracted three times with EtOAc. The combined organics were dried over Na2SO4, concentrated, and subjected to silica gel chromatography using EtOAc-heptane as the eluant to provide Compound [LXII]: 1H NMR (400 MHz, METHANOL-d4) δ ppm 3.54-3.66 (m, 2H) 4.66 (dd, J=6.76, 5.10 Hz, 1H) 7.24-7.35 (m, 2H) 7.41-7.53 (m, 2H).

Workup

  1. extractionextracted three times with EtOAc
  2. dry with materialThe combined organics were dried over Na2SO4
  3. concentrationconcentrated
  4. customto provide Compound [LXII]

Sources & evidence

ORD record
ord-540b65ed130f48c8aba26cb93484e3f3
Source dataset
uspto-grants-2013_12
Patent number
US08614221B2

Reaction notes

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