m-Fluorobenzenethiol → HCID 69006946, compound

HRID 1432040Notes

Reaction equation

HRID 1432040 reaction equation
CC([O-])(C)C.[K+].[Cl:7][C:8]1[CH:9]=[CH:10][C:11](I)=[C:12]([O:14][CH3:15])[CH:13]=1.C1C=CC(P(C2C(OC3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=CC=3)=CC=CC=2)C2C=CC=CC=2)=CC=1.[F:56][C:57]1[CH:58]=[C:59]([SH:63])[CH:60]=[CH:61][CH:62]=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]>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([S:63][C:59]2[CH:60]=[CH:61][CH:62]=[C:57]([F:56])[CH:58]=2)=[C:12]([O:14][CH3:15])[CH:13]=1

Participants

6

Reactant 4

HCID 75710m-FluorobenzenethiolHCID 4285986Bis[2-(diphenylphosphino)phenyl] etherHCID 160792304-Chloro-1-iodo-2-methoxybenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 69006946HCID 69006946, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
95 °C

Procedure

A dry round bottomed flask was charged with KOtBu (1.903 g, 17.0 mmol), 5-chloro-2-iodoanisole (4.054 g, 15.1 mmol), Pd2dba3 (144 mg, 0.16 mmol), DPEPhos (176 mg, 0.33 mmol) and 3-fluoro-thiophenol (1.903 g, 17.0 mmol). The flask was evacuated and backfilled with Ar three times. Dry toluene (80 mL) was added and the mixture stirred at 95° C. for 2 h. The mixture was filtered through a pad of silica gel followed by adsorption onto silica gel. After purification by flash chromatography using silica gel, eluting with heptanes/EtOAc, 97:3, the title compound was obtained as a yellow oil (3.41 g, 85%).

Workup

  1. customThe flask was evacuated
  2. additionDry toluene (80 mL) was added
  3. filtrationThe mixture was filtered through a pad of silica gel
  4. customAfter purification by flash chromatography
  5. washeluting with heptanes/EtOAc, 97:3

Sources & evidence

ORD record
ord-d9a7e3b251344f4c873a2ca7444263e2
Source dataset
uspto-grants-2009_11
Patent number
US07612068B2

Reaction notes

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