1-Chloro-4-(trifluoromethyl)benzene → HCID 67387269, compound

HRID 1465634Notes

Reaction equation

HRID 1465634 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[OH:20][C:21]1[CH:26]=[C:25]([CH3:27])[C:24]([C:28](=[O:30])[CH3:29])=[C:23]([CH3:31])[CH:22]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:31][C:23]1[CH:22]=[C:21]([O:20][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=2)[CH:26]=[C:25]([CH3:27])[C:24]=1[C:28](=[O:30])[CH3:29]

Participants

7

Reactant 4

HCID 73941-Chloro-4-(trifluoromethyl)benzeneHCID 62657Potassium Phosphate, TribasicHCID 40573701-(4-Hydroxy-2,6-dimethylphenyl)ethanoneHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphane

Product 1

HCID 67387269HCID 67387269, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 1-chloro-4-(trifluoromethyl)benzene (6.60 g, 36.6 mmol), K3PO4 (12.9 g, 60.9 mmol), 1-(4-hydroxy-2,6-dimethylphenyl)ethanone (5.00 g, 30.5 mmol) in toluene (60.9 mL) was added 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (388 mg, 0.91 mmol) and Pd(OAc)2 (288 mg, 1.28 mmol). The reaction was heated at 100° C. for 120 min under N2. The solution was cooled to room temperature and filtered through a small pad of diatomaceous earth. The cake was washed with ethyl acetate (50 mL) and combined filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to give 1-(2,6-dimethyl-4-(4-(trifluoromethyl)phenoxy)phenyl)ethanone (1.8 g) as yellow oil in 19% yield: 1H NMR (500 MHz, CDCl3) δ 7.58 (d, J=8.5 Hz, 2 H), 7.04 (d, J=8.5 Hz, 2 H), 6.70 (s, 2 H), 2.50 (s, 3 H), 2.25 (s, 6H).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. filtrationfiltered through a small pad of diatomaceous earth
  3. washThe cake was washed with ethyl acetate (50 mL)
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-6e228307d96f47f5b32fe8a33bd23200
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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