Diisopropylethylamine → HCID 117703943, compound

HRID 1049878Notes

Reaction equation

HRID 1049878 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[F:12].CCN(C(C)C)C(C)C.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[CH2:64]([CH:66]([CH2:74][CH2:75][CH2:76][CH3:77])[CH2:67][O:68][C:69](=[O:73])[CH2:70][CH2:71][SH:72])[CH3:65]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:64]([CH:66]([CH2:74][CH2:75][CH2:76][CH3:77])[CH2:67][O:68][C:69](=[O:73])[CH2:70][CH2:71][S:72][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[F:12])[CH3:65]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 926402-Ethylhexyl 3-mercaptopropionateHCID 1424144-Bromo-3-fluorobenzotrifluorideHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 117703943HCID 117703943, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of 1-bromo-2-fluoro-4-trifluoromethyl-benzene (5.0 g, 20.6 mmol) and DIEA (7.2 mL, 41.1 mmol) in toluene (100 mL) is degased under N2 atmosphere. To this mixture, Pd2 dba3 (753 mg, 0.82 mmol), Xantphos (952 mg, 1.65 mmol) and 3-mercapto-propionic acid 2-ethyl-hexyl ester (5.9 mL, 25.7 mmol) are added and the reaction is heated at reflux overnight. The resulting mixture is filtered over a plug of silica (EtOAc) and the organic is concentrated in vacuo. Purification by silica chromatography (EtOAc/petroleum ether; 3:97) affords the desired product.

Workup

  1. temperaturethe reaction is heated
  2. temperatureat reflux overnight
  3. filtrationThe resulting mixture is filtered over a plug of silica (EtOAc)
  4. concentrationthe organic is concentrated in vacuo
  5. customPurification by silica chromatography (EtOAc/petroleum ether; 3:97)

Sources & evidence

ORD record
ord-1b3c02bc59af4a2eb909cdd73e31cffd
Source dataset
uspto-grants-2016_07
Patent number
US09382254B2

Reaction notes

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