Toluene → 1-Fluoro-3-methoxy-5-((4-methoxybenzyl)sulfanyl)benzene

HRID 591558Notes

Reaction equation

HRID 591558 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([F:10])[CH:3]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][SH:20])=[CH:15][CH:14]=1.C1(C)C=CC=CC=1.CCN(C(C)C)C(C)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].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.O>[F:10][C:4]1[CH:3]=[C:2]([S:20][CH2:19][C:16]2[CH:17]=[CH:18][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 804074-Methoxy-alpha-toluenethiolHCID 81531DiisopropylethylamineHCID 108220943-Bromo-5-fluoroanisole

Product 1

HCID 897678621-Fluoro-3-methoxy-5-((4-methoxybenzyl)sulfanyl)benzeneYield 91.4%

Reagents, catalysts & solvents 3

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolvent

Procedure

To a mixture of 1-bromo-3-fluoro-5-methoxybenzene (5 g), (4-methoxyphenyl)methanethiol (3.76 g), and toluene (100 mL) were added Pd2(dba)3 (0.447 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.564 g) and DIPEA (8.52 mL). The mixture was stirred at room temperature overnight. The mixture was poured into water and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (6.20 g).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed successively with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-913009ee3728439fb3464c42344a6a54
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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