4-Methoxy-alpha-toluenethiol → HCID 86729450, compound

HRID 1507039Notes

Reaction equation

HRID 1507039 reaction equation
Br[C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][SH:24])=[CH:19][CH:18]=1.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.CCN(C(C)C)C(C)C>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.[Pd].[Pd]>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][S:24][C:2]2[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=2[O:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 804074-Methoxy-alpha-toluenethiolHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 3310995ethyl 2-(2-bromophenoxy)acetate

Product 1

HCID 86729450HCID 86729450, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 2-(2-bromophenoxy)acetate (3.0 g, 0.0116 mol) in dioxane (30 mL) was added (4-methoxyphenyl)methanethiol (2.14 g, 0.0139 mol), Pd2(dba)3 (20 mg), xantphos (20 mg) and DIEA (3 mL). The mixture was degassed 4 times (N2) and heated at reflux for 3 h, concentrated, and the crude product was purified by column chromatography. (3 g, yield 79%) MS (ESI+) e/z: 355.1 [M+1]+.

Workup

  1. customThe mixture was degassed 4 times (N2)
  2. temperatureheated
  3. temperatureat reflux for 3 h
  4. concentrationconcentrated
  5. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-98574e6db942453ebcd0808ff0a71a47
Source dataset
uspto-grants-2015_12
Patent number
US09221794B2

Reaction notes

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