3-Bromo-N-methoxy-N-methylbenzamide → 1-Butanone, 1-(3-bromophenyl)-4,4,4-trifluoro-

HRID 30561Notes

Reaction equation

HRID 30561 reaction equation
[F:1][C:2]([CH2:5][CH3:6])([F:4])[F:3].[Br-].[Mg+2].[Br-].[Br:10][C:11]1[CH:12]=[C:13]([CH:20]=[CH:21][CH:22]=1)[C:14](N(OC)C)=[O:15]>C1COCC1>[Br:10][C:11]1[CH:12]=[C:13]([C:14](=[O:15])[CH2:6][CH2:5][C:2]([F:4])([F:3])[F:1])[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 121628753-Bromo-N-methoxy-N-methylbenzamideHCID 86611664HCID 86611664, compound

Product 1

HCID 574358661-Butanone, 1-(3-bromophenyl)-4,4,4-trifluoro-Yield 77.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A prepared solution of trifluoromethyl ethane-magnesium bromide (made by refluxing Mg with 1-bromo, 2-trifluoromethyl ethane in THF for 2 hours; 4.6 g=25.82 mmol) in THF was added slowly to a cold (0° C.) solution of 3-bromo-N-methoxy-N-methylbenzamide (3.5 g, 14.3 mmol) in THF. The stirring continued at room temperature for 1 hour, quenched with cold saturated aqueous NH4Cl, acidified with 1 N HCl and extracted with ethyl ether. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo. The crude product was purified on silica gel (ISCO) using hexanes/EtOAc (10/1) as the eluting solvent to give 1-(3-Bromo-phenyl)-4,4,4-trifluoro-butan-1-one as a colorless oil (3.1 g, 77% yield). m/e (M−H)− 279, 1H NMR (400 MHz, DMSO-d6) δ ppm, 2.5-2.6 (m, 2 H), 3.3-3.4 (m, 2 H), 7.5 (t, J=7.9 Hz, 1 H), 7.8-7.8 (m, 1 H), 7.9-8.0 (m, 1 H), 8.1 (t, J=1.7 Hz, 1 H).

Workup

  1. customquenched with cold saturated aqueous NH4Cl
  2. extractionextracted with ethyl ether
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified on silica gel (ISCO)

Sources & evidence

ORD record
ord-52a69ff2e7d944c3aa9d3d36699fd04b
Source dataset
uspto-grants-2008_09
Patent number
US07423158B2

Reaction notes

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