Toluene → HCID 86642186, compound

HRID 1848301Notes

Reaction equation

HRID 1848301 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C:13](O)([C:25]([F:28])([F:27])[F:26])[CH2:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([Cl:24])[CH:18]=2)=[O:16])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C1(C)C=CC=CC=1.C(OC(=O)C)(=O)C>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[F:30][C:2]([F:1])([F:31])[C:3]1[CH:4]=[C:5]([C:13]([C:25]([F:28])([F:27])[F:26])=[CH:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([Cl:24])[CH:18]=2)=[O:16])[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 7918Acetic AnhydrideHCID 86642187HCID 86642187, compound

Product 1

HCID 86642186HCID 86642186, compoundYield 98.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
70 °C

Procedure

1.15 g of 3-(3,5-bis(trifluoromethyl)phenyl)-1-(3-chloro-4-methylphenyl)-4,4,4-trifluoro-3-hydroxybutan-1-one, 2.3 g of toluene, 0.49 g of acetic anhydride, 29 mg of 4-dimethylaminopyridine and 0.38 g of pyridine were fed, and stirred for 9 hours at 70° C. The mixture was cooled to room temperature, and separated by adding 5 ml of toluene, iced water and 0.6 ml of concentrated hydrochloric acid. The organic phase was washed with water, and the solvent was distilled off under reduced pressure. The obtained residue was roughly purified by using a small amount of silica gel to obtain 1.09 g of 3-(3,5-bis(trifluoromethyl)phenyl)-1-(3-chloro-4-methylphenyl)-4,4,4-trifluoro-2-buten-1-one as yellow liquid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customseparated
  3. additionby adding 5 ml of toluene, iced water and 0.6 ml of concentrated hydrochloric acid
  4. washThe organic phase was washed with water
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe obtained residue was roughly purified

Sources & evidence

ORD record
ord-f2aeb64c6034453bb6f77f12098e080b
Source dataset
uspto-grants-2015_02
Patent number
US08952175B2

Reaction notes

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