Thiophenol → HCID 66735902, compound

HRID 1641575Notes

Reaction equation

HRID 1641575 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]3([CH2:22][O:23][P:24]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:26]([CH3:29])([CH3:28])[CH3:27])=[O:25])[CH2:20][O:19][C:18]([CH3:21])=[N:17]3)=[CH:10][CH:9]=2)=[C:4]([F:34])[CH:3]=1.[C:35]1([SH:41])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(N(C(C)C)CC)(C)C.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1.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.C(Cl)(Cl)Cl.[Pd].[Pd].O>[F:34][C:4]1[CH:3]=[C:2]([S:41][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:7]=[CH:6][C:5]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][C:16]2([CH2:22][O:23][P:24]([C:30]([CH3:33])([CH3:32])[CH3:31])([C:26]([CH3:29])([CH3:28])[CH3:27])=[O:25])[CH2:20][O:19][C:18]([CH3:21])=[N:17]2)=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 7969ThiophenolHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 66736357HCID 66736357, compound

Product 1

HCID 66735902HCID 66735902, compoundYield 48.7%

Reagents, catalysts & solvents 3

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4-[2-(4′-bromo-2′-fluorobiphenyl-4-yl)ethyl]-4-di(tert-butyl)phosphoryloxymethyl-2-methyl-2-oxazoline (201 mg), benzenethiol (42 mg), diisopropylethylamine (89 mg), tris(dibenzylideneacetone)dipalladium(0) chloroform adduct (17.8 mg) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos) (19.9 mg) in 1,4-dioxane (2 mL) was heated under reflux for 15 hr under a nitrogen atmosphere. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound (103 mg) as a yellow oil.

Workup

  1. temperatureunder reflux for 15 hr under a nitrogen atmosphere
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-045dc7052e0542bb85669b530d7801f0
Source dataset
uspto-grants-2012_02
Patent number
US08114902B2

Reaction notes

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