Diethyl Ether → HCID 13355716, compound

HRID 2211902Notes

Reaction equation

HRID 2211902 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[C:6]([F:14])[CH:5]=1)(=[O:3])[CH3:2].[Br:15]Br.C(OCC)C>C(Cl)(Cl)Cl.C(O)C>[Br:15][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:13])[CH3:12])=[C:6]([F:14])[CH:5]=1)=[O:3]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 24408BromineHCID 3020368N-(4-Acetyl-2-fluorophenyl)acetamide

Product 1

HCID 13355716HCID 13355716, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

N-(4-Acetyl-2-fluoro-phenyl)-acetamide (3.55 g, 18.2 mmol) was dissolved in boiling chloroform (100 mL). Under reflux conditions, a solution of bromine (0.86 mL, 17.5 mmol) in chloroform (20 mL) was added. The reaction mixture was refluxed for an additional 20 min. then cooled, concentrated to give an orange residue. The residue was taken up in ethanol (50 mL) and then diethyl ether (20 mL) was added and the resulting solution cooled to 0° C. A yellow solid precipitated over 48 h and was collected by filtration, washed with cold ethanol (10 mL) and dried to give 2.40 g (8.77 mmol) of the desired product as a yellow powder. Yield: 48.2%; mp 184° C.; 1H NMR (400 MHz, DMSO-d6) δ 10.15 (s, 1H, NH, 8.29 (t, J=8.0 Hz, 1H), 7.88–7.83 (m, 2H), 4.90 (s, 2H, CH2), 2.17 (s, 3H, Me).

Workup

  1. temperatureThe reaction mixture was refluxed for an additional 20 min.
  2. temperaturethen cooled
  3. concentrationconcentrated
  4. customto give an orange residue
  5. customA yellow solid precipitated over 48 h
  6. filtrationwas collected by filtration
  7. washwashed with cold ethanol (10 mL)
  8. customdried

Sources & evidence

ORD record
ord-65d4b9a6c0f640baac5dbac22bef2d7f
Source dataset
uspto-grants-2006_09
Patent number
US07101886B2

Reaction notes

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