Chlorine → 4-(5-Chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-one

HRID 400617Notes

Reaction equation

HRID 400617 reaction equation
[O:1]1[C:5]2[C:6]([C:10]([CH3:19])([CH3:18])[CH2:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1.[Cl:20]Cl>C(O)(=O)C>[Cl:20][C:8]1[CH:7]=[C:6]([C:10]([CH3:19])([CH3:18])[CH2:11][C:12](=[O:17])[C:13]([F:15])([F:16])[F:14])[C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=1

Participants

4

Reactant 2

HCID 24526Chlorine3×HCID 469392134-(2,3-Dihydrobenzofur-7-yl)-1,1,1-trifluoro-4-methyl-2-pentanone

Product 1

HCID 469392144-(5-Chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of 4-(2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-one (20.8 g, 76.2 mmol) in 200 mL of acetic acid was treated with a solution of chlorine gas (Cl2) in acetic acid (prepared by bubbling chlorine gas into acetic acid, ˜1.19 M). The reaction was monitored by 1H-NMR. The ratio of the starting material to product was determined based on the integration of CH2 signal of the respective ketones (starting material: δ=3.32 ppm; product: δ=3.32 ppm). The concentration of the Cl2 solution was recalculated based on the NMR ratios and an additional portion of Cl2 solution was added (this process was repeated until NMR showed the complete consumption of the starting material). The mixture was quenched with 500 mL of water and solid sodium bicarbonate (˜500 g) was added carefully during 1 hour. The mixture was poured onto 500 mL of ethyl acetate. The phases were separated and the aqueous layer was extracted with three 500 mL portions of ethyl acetate. The combined organic layers were washed with two 100 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 23.4 g of the title product (quantitative yield), which was used without purification.

Workup

  1. customthe complete consumption of the starting material)
  2. customThe mixture was quenched with 500 mL of water and solid sodium bicarbonate (˜500 g)
  3. additionwas added carefully during 1 hour
  4. additionThe mixture was poured onto 500 mL of ethyl acetate
  5. customThe phases were separated
  6. extractionthe aqueous layer was extracted with three 500 mL portions of ethyl acetate
  7. washThe combined organic layers were washed with two 100 mL portions of brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8bb2be9396db4b9d9c94350b16e56bb0
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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