Acetone → HCID 86603894, compound

HRID 1171176Notes

Reaction equation

HRID 1171176 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([Cl:9])[C:3]=1[Cl:10].C(=O)([O-])[O-].[K+].[K+].[CH3:17][C:18]([CH3:20])=[O:19]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:17][CH:18]2[CH2:20][O:19]2)=[C:4]([Cl:9])[C:3]=1[Cl:10]

Participants

4

Reactant 3

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 123115384-Bromo-2,3-Dichlorophenol

Product 1

HCID 86603894HCID 86603894, compoundYield 71%

Procedure

A solution of the crude 4-bromo-2,3-dichlorophenol (7.96 g) and (2R)-glycidyl 3-nitrobenzenesulfonate (8.52 g) in dry acetone (250 mL) was treated with potassium carbonate (13.61 g) and refluxed under nitrogen for 12 h. The reaction was cooled, filtered and filtrate was concentrated in vacuo and the residue was flash chromatographed (20% ethyl acetate/hexanes) to yield the desired product (6.94 g) in 71% yield. 1H-NMR (400 MHz, CDCl3) δ: 7.48 and 6.82 (d, 2H), 4.37 and 4.34 (dd, 1H), 4.06 and 4.03 (dd, 1H), 3.42-3.39 (m, 1H), 2.96-2.94 (m, 1H), 2.85-2.83 (m, 1H).

Workup

  1. temperaturerefluxed under nitrogen for 12 h
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. concentrationfiltrate was concentrated in vacuo
  5. customchromatographed (20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-670e9600fbbf4165abc34dc7a5d116a8
Source dataset
uspto-grants-2010_11
Patent number
US07829594B2

Reaction notes

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