Chloroacetone → 1-(3-Bromo-4-fluorophenylthio)propan-2-one

HRID 523575Notes

Reaction equation

HRID 523575 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[CH:6][C:7]=1[F:8].Cl[CH2:11][C:12](=[O:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([S:9][CH2:11][C:12](=[O:14])[CH3:13])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 265970903-Bromo-4-Fluorothiophenol

Product 1

HCID 667645651-(3-Bromo-4-fluorophenylthio)propan-2-oneYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using analogous reagents and reaction conditions as described in Example 24 for the preparation of I-24a above, 3-bromo-4-fluoro-benzenethiol (2.0 g, 9.756 mmol) was reacted with 1-chloro-propan-2-one (0.86 mL, 10.73 mmol), DMF (6.0 mL), and potassium carbonate (2.69 g, 19.51 mmol) to afford crude product which was purified by column on silica gel (5% ethyl acetate in hexane) to afford 2.1 g of the product (82% yield).

Workup

  1. customreagents and reaction conditions
  2. customto afford crude product which
  3. customwas purified by column on silica gel (5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-48037dd1bf4f49cdbfd4f9ecd5168ec3
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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