Benzene, 1-bromo-4-(trifluoromethyl)- → HCID 58118066, compound

HRID 1047383Notes

Reaction equation

HRID 1047383 reaction equation
Br[C:2]1C=CC(C(F)(F)F)=CC=1.[CH2:12]([O:14][C:15]([CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)[C:31]=2[C:40]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)C=C[C:41]=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].ClCCl>[CH2:12]([O:14][C:15]([CH:17]1[CH2:22][CH2:21][N:20]([C:46]2[CH:47]=[CH:48][C:49]([C:40]([CH3:31])([CH3:41])[CH3:2])=[CH:44][CH:45]=2)[CH2:19][CH2:18]1)=[O:16])[CH3:13]

Participants

9

Reactant 4

HCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-HCID 70770Ethyl 4-piperidinecarboxylateHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Product 1

HCID 58118066HCID 58118066, compoundYield 200%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Bromobenzotrifluoride (572 μL, 3.30 mmol), piperidine-4-carboxylic acid ethyl ester (985 μL, 6.00 mmol), tris-(dibenzylideneacetone)-dipalladium (62 mg, 0.07 mmol), 2,2′-bis-(diphenylphosphino)-1,1′-binaphthalin (121 mg, 0.19 mmol), and sodium tert-butoxide (576 mg, 6.0 mmol) were dissolved in toluene (5 mL). The resulting mixture was irradiated at 120° C. for 30 min in a microwave oven. The mixture was then cooled to room temperature and diluted with ethyl acetate (20 mL). This resulted in a precipitate. The precipitate was separated by filtration, and the filtrate was concentrated under vacuum. Purification by column chromatography on silica gel (dichloromethane/diethylether; first eluting with a 1:0 mixture (i.e., all dichloromethane), and then with a 6:1 mixture) afforded the desired product as an oil (110 mg, 12% yield).

Workup

  1. customThe resulting mixture was irradiated at 120° C. for 30 min in a microwave oven
  2. customThis resulted in a precipitate
  3. customThe precipitate was separated by filtration
  4. concentrationthe filtrate was concentrated under vacuum
  5. customPurification by column chromatography on silica gel (dichloromethane/diethylether
  6. washfirst eluting with a 1:0 mixture (i.e.

Sources & evidence

ORD record
ord-e9b669b4d95d4f119f840486febbc392
Source dataset
uspto-grants-2013_10
Patent number
US08569495B2

Reaction notes

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