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

HRID 2387298Notes

Reaction equation

HRID 2387298 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 24526ChlorineHCID 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-oneYield 100%

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 in acetic acid (˜1.19 M). The reaction was monitored by 1H-NMR. 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 4-(5-chloro-2,3-dihydrobenzofuran-7-yl)-1,1,1-trifluoro-4-methylpentan-2-one (100%), which was used without purification.

Workup

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

Sources & evidence

ORD record
ord-8cdc91c7a1d24d10a09f676c5a07183c
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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