Chloroacetone → HCID 22144837, compound

HRID 558137Notes

Reaction equation

HRID 558137 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].C([O-])([O-])=O.[K+].[K+].Cl[CH2:17][C:18](=[O:20])[CH3:19]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:17][C:18](=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 6054722-Bromo-4-fluorophenol

Product 1

HCID 22144837HCID 22144837, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cool a suspension of 2-bromo-4-fluoro-phenol (1 g, 4.89 mmol) and K2CO3 (1.8 g, 13.2 mmol) in DMF (10 mL) to 0° C. in an ice bath under nitrogen. Add chloroacetone (678 mg, 7.33 mmol) during a period of 30 min. Stir the mixture at RT overnight. Add water and extract with ethyl acetate. Wash the solution with aqueous saturated sodium chloride. Dry over sodium sulfate. Concentrate the solution in vacuo. Purify by column chromatography (hexane to 10% ethyl acetate in hexane) to give the title compound as a yellow oil (0.75 g, 59%). 1H NMR (400 MHz-CDCl3) δ 2.35 (s, 3H), 4.51 (s, 2H), 6.73 (dd, J=4.8, 8.8 Hz, 1H), 6.97 (m, 1H), 7.32 (m, 1H).

Workup

  1. temperatureCool
  2. extractionAdd water and extract with ethyl acetate
  3. washWash the solution with aqueous saturated sodium chloride
  4. dry with materialDry over sodium sulfate
  5. concentrationConcentrate the solution in vacuo
  6. customPurify by column chromatography (hexane to 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-49c7607cbeac410db5aef86e3750cd52
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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