Tris(propan-2-yl)silanethiol → 5-Methyl-2-triisopropylsilanylsulfanyl-benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2OC2C=CC=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[Na+].[CH:58]([Si:61]([CH:66]([CH3:68])[CH3:67])([CH:63]([CH3:65])[CH3:64])[SH:62])([CH3:60])[CH3:59]>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(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[S:62][Si:61]([CH:63]([CH3:65])[CH3:64])([CH:66]([CH3:68])[CH3:67])[CH:58]([CH3:59])[CH3:60]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 150 °C
Procedure
2-Bromo-5-methyl-benzoic acid methyl ester (2.06 g, 9.00 mmol), tris(dibenzylideneacetone)dipalladium (0) (83 mg, 0.09 mmol), bis(2-diphenylphosphinophenyl)ether (97 mg, 0.18 mmol), sodium tert-butoxide (1.00 g, 10.4 mmol), triisopropylsilanethiol (1.37g, 7.2 mmol) and dry toluene (10 mL) are all placed in an Emrys Optimizer EXP 20 mL microwave reactor tube. The reaction vessel is sealed and subjected to microwave heating at 150° C. for 30 minutes. Upon cooling the mixture is poured onto a plug of silica and the product is eluted with ethyl acetate-heptane (2:8). This furnishes the title compound as an oil, which is used in the next step without further purification.
Workup
- customThe reaction vessel is sealed
- temperatureUpon cooling the mixture
- additionis poured onto a plug of silica
- washthe product is eluted with ethyl acetate-heptane (2:8)
Sources & evidence
- ORD record
- ord-957c6824786e44e19419b8b615b23c46
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07534791B2
Reaction notes
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