Benzene, 1-bromo-3-(trifluoromethyl)- → HCID 20073070, compound

HRID 1414579Notes

Reaction equation

HRID 1414579 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:6][CH:7]=1.[Mg].[CH:13]1([C:16](=[O:24])[CH2:17][CH2:18][N:19]([CH3:23])[C:20](=[O:22])[CH3:21])[CH2:15][CH2:14]1.[Cl-].[NH4+]>O.CCOCC.CC(=O)C>[CH:13]1([C:16]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=2)([OH:24])[CH2:17][CH2:18][N:19]([CH3:23])[C:20](=[O:22])[CH3:21])[CH2:15][CH2:14]1

Participants

8

Reactant 4

HCID 9817Benzene, 1-bromo-3-(trifluoromethyl)-HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 21488089HCID 21488089, compound

Product 1

HCID 20073070HCID 20073070, compound

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

An ether solution of a Grignard reagent prepared from 50.0 g. (0.35 mole) of 3-bromobenzotrifluoride, 400 ml. of ether and 8.6 g. (0.354 mole) of magnesium was treated at -20° C to -30° C. with 12.5 g. (0.059 mole) of crude 1-cyclopropyl-3-(N-methylacetamido)-1-propanone (calculated to contain 80% of the propanone by the nuclear magnetic resonance spectrum) in 100 ml. of ether. The rection mixture was warmed to room temperature and treated with 7.4 g. (0.14 mole) ammonium chloride followed by 20 ml. of water. The ether layer was separated, concentrated to a dark oil and distilled under reduced pressure. The yield was 6.2 g.; b.p. 110°-114° C./0.1 mm.

Workup

  1. additiontreated with 7.4 g
  2. customThe ether layer was separated
  3. concentrationconcentrated to a dark oil
  4. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-9883ec48deb342639277af4c5a4a188a
Source dataset
uspto-grants-1977_01
Patent number
US04001429

Reaction notes

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