4-Methoxy-alpha-toluenethiol → 3-Fluoro-5-(4-methoxy-benzylsulfanyl)-benzoic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7](Br)[CH:6]=1)[CH3:2].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.[CH3:56][O:57][C:58]1[CH:65]=[CH:64][C:61]([CH2:62][SH:63])=[CH:60][CH:59]=1.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]>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:6]=[C:7]([S:63][CH2:62][C:61]2[CH:64]=[CH:65][C:58]([O:57][CH3:56])=[CH:59][CH:60]=2)[CH:8]=[C:9]([F:11])[CH:10]=1)[CH3:2]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
To a room temperature, degassed solution of 3-Bromo-5-fluoro-benzoic acid ethyl ester (4.0 g, 16.2 mmol) in dioxane (100 mL) was added 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.48 g, 0.82 mmol), 4-methoxy-benzylmercaptan (2.26 mL, 16.2 mmol), DIEA (5.6 mL, 32.4 mmol), and tris(dibenzylideneacetone)dipalladium(0) (0.37 g, 0.41 mmol). The resulting mixture was warmed to 90° C. and stirred for 2 hrs, then cooled to room temperature. The mixture was subjected to standard aqueous workup, and the crude residue was filtered through a pad of silica gel to afford the title compound.
Workup
- temperaturecooled to room temperature
- filtrationthe crude residue was filtered through a pad of silica gel
Sources & evidence
- ORD record
- ord-45e8d9b22f70431bad99d4a81f6b0988
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09000025B2
Reaction notes
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