Acetone → 2-(4-Bromophenyl)-3,3,3-trifluoro-1,2-propanediol

HRID 1972435Notes

Reaction equation

HRID 1972435 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([F:13])([F:12])[F:11])=[CH2:9])=[CH:4][CH:3]=1.C[N+]1([O-])CC[O:18]CC1.CC(C)=O.[O-]S([O-])=O.[Na+].[Na+].[OH2:32]>[Os](=O)(=O)(=O)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:18])([C:10]([F:11])([F:12])[F:13])[CH2:9][OH:32])=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 180AcetoneHCID 962WaterHCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 665824581-Bromo-4-(3,3,3-trifluoroprop-1-en-2-yl)benzene

Product 1

HCID 665825852-(4-Bromophenyl)-3,3,3-trifluoro-1,2-propanediol

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

Osmium tetroxide (4 wt % solution with water, 4.3 mL, 0.70 mmol) was added to a stirring mixture of 1-bromo-4-(1-(trifluoromethyl)ethenyl)benzene (3.5 g, 14 mmol), 4-methylmorpholine N-oxide (1.8 g, 15 mmol), acetone (14 mL), and water (14 mL) at room temperature. After 21 h, Na2SO3 (8.8 g, 70 mmol) was added, the mixture was filtered. Silica gel (20 g) was added to the filtrate, and the volatiles were removed in vacuo. The residue was purified via column chromatography (5% MeOH in CH2Cl2) to afford 2-(4-bromophenyl)-3,3,3-trifluoro-1,2-propanediol (3.0 g) as an off-white solid.

Workup

  1. filtrationthe mixture was filtered
  2. additionSilica gel (20 g) was added to the filtrate
  3. customthe volatiles were removed in vacuo
  4. customThe residue was purified via column chromatography (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-80f57a28241e49e4bb03feedcd2411af
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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