Thiophenol → HCID 12551991, compound

HRID 625707Notes

Reaction equation

HRID 625707 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:11].[C:12]1([SH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.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.C(N(CC)C(C)C)(C)C>O1CCOCC1>[C:12]1([S:18][C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2[CH2:4][CH2:5][C:6]3=[O:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 81531DiisopropylethylamineHCID 987131-Indanone, 4-bromo-HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 12551991HCID 12551991, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Bromo-1-indanone (0.30 g), thiophenol (0.15 mL), tris(dibenzylideneacetone)palladium(0) (0.13 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.082 g) and N,N-diisopropylethylamine (0.98 mL) are stirred in dioxane (1 mL) for 2 hours under microwave irradiation at 120° C. After removal of the solvent under vacuum the residue is purified by column chromatography (silica gel, cyclohexane:ethyl acetate 6:4) to give the desired material (0.34 g). LC (METHOD 5): tR=1.28 min; Mass spectrum: m/z=241 [M+H]+.

Workup

  1. customAfter removal of the solvent under vacuum the residue
  2. customis purified by column chromatography (silica gel, cyclohexane:ethyl acetate 6:4)

Sources & evidence

ORD record
ord-2d7233cae0fb4064bc5086e63433b67d
Source dataset
uspto-grants-2016_04
Patent number
US09308194B2

Reaction notes

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