3-Bromo-1,1,1-trifluoro-2-propanone → HCID 19047036, compound

HRID 1780591Notes

Reaction equation

HRID 1780591 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([C:8](=[S:10])[NH2:9])[CH:7]=1.Br[CH2:15][C:16](=[O:21])[C:17]([F:20])([F:19])[F:18].C(OCC)(=O)C.CCCCCC>C(O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([C:8]2[S:10][CH2:15][C:16]([C:17]([F:20])([F:19])[F:18])([OH:21])[N:9]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 19047049HCID 19047049, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 19047036HCID 19047036, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product from Step B (5.5 g, 0.028 mol) was dissolved in ethyl alcohol (100 mL). 3-bromo-1,1,1-trifluoroacetone (5.3 g, 0.028 mol) was added and the resulting solution refluxed for 3 h. After cooling to room temperature, the reaction mixture was evaporated to dryness. The residue was partitioned between ethyl acetate and 10% aqueous sodium carbonate (200 mL each). The organic layer was separated, dried (MgSO4) and then concentrated to give an oil. Flash chromatography of this oil on silica gel eluting with 20% ethyl acetate/hexane afforded a solid which was further purified by recrystallization from chlorobutane/hexane. Yield: 4.4 g (51%) of the title compound as a white solid melting at 148°-151° C. 1H NMR (300 MHz, CDCl3) δ 7.96-7.98 (m,1H), 7.42-7.44 (m,2H), 3.86-3.89 (m,1H), 3.34 (s,1H), 2.49 (s,3H).

Workup

  1. temperaturethe resulting solution refluxed for 3 h
  2. customthe reaction mixture was evaporated to dryness
  3. customThe residue was partitioned between ethyl acetate and 10% aqueous sodium carbonate (200 mL each)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto give an oil
  8. customwas further purified by recrystallization from chlorobutane/hexane

Sources & evidence

ORD record
ord-3a32b289d6d449afb5cb6c4a17ede794
Source dataset
uspto-grants-1997_05
Patent number
US05631206

Reaction notes

Loading…