1-(3,5-Bis(trifluoromethyl)phenyl)ethan-1-one → 3,5-Bis(trifluoromethyl)phenacyl bromide

HRID 2298613Notes

Reaction equation

HRID 2298613 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([C:14]([F:17])([F:16])[F:15])[CH:5]=1)=[O:3].C=CC1C=C[NH+]=CC=1.[Br-:26].[Br-].[Br-]>CO>[F:17][C:14]([F:15])([F:16])[C:6]1[CH:5]=[C:4]([C:2](=[O:3])[CH2:1][Br:26])[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=1

Participants

4

Reactant 2

HCID 1216161-(3,5-Bis(trifluoromethyl)phenyl)ethan-1-oneHCID 18537368HCID 18537368, compound

Product 1

HCID 27361703,5-Bis(trifluoromethyl)phenacyl bromideYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A stirred suspension of 1 g (3.9 mmol) of 3,5-bis(trifluoromethyl)acetophenone (Lancaster, Windham, N.H., USA) in dry methanol (20 mL) and 1 g (15 mmol, 2.6 eq) of poly(4-vinyl pyridinium tribromide)(Aldrich, Milwaukee, Wis. , USA) was protected from moisture with dry nitrogen, and heated at reflux for 70 min. The polymer was filtered from the cooled solution and washed with methanol and twice with dichloromethane. The solvents were removed in vacuo to give 1-[3,5-bis(trifluoromethyl)phenyl]-2-bromoethan-1-one (1.2 g, 92%). 1H-NMR (DMSO-d6; 300 MHz) δ8.43 (m, 2H), 8.12 (m, 1H), 4.46 (s, 3H).

Workup

  1. temperatureheated
  2. temperatureat reflux for 70 min
  3. filtrationThe polymer was filtered from the cooled solution
  4. washwashed with methanol and twice with dichloromethane
  5. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-720739c67ddb452e87c521ad9f0af77c
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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