Sodium hydride → 4-Methyl-3-triisopropylsilanylsulfanyl-benzoic acid ethyl ester

HRID 1466839Notes

Reaction equation

HRID 1466839 reaction equation
[CH:1]([Si:4]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[SH:5])([CH3:3])[CH3:2].[H-].[Na+].Br[C:15]1[CH:16]=[C:17]([CH:23]=[CH:24][C:25]=1[CH3:26])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:21]([O:20][C:18](=[O:19])[C:17]1[CH:23]=[CH:24][C:25]([CH3:26])=[C:15]([S:5][Si:4]([CH:1]([CH3:3])[CH3:2])([CH:6]([CH3:8])[CH3:7])[CH:9]([CH3:11])[CH3:10])[CH:16]=1)[CH3:22]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 3435097Tris(propan-2-yl)silanethiolHCID 14945865Ethyl 3-bromo-4-methylbenzoate

Product 1

HCID 667648104-Methyl-3-triisopropylsilanylsulfanyl-benzoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. stirred solution of triisopropylsilanethiol (14.28 mmol, 3.07 mL) in THF was added sodium hydride (14.28 mmol, 0.57 g of a 60 wt % dispersion in mineral oil). After 30 min, the mixture was added to a solution of ethyl 3-bromo-4-methylbenzoate (10.99 mmol, 2.67 g) at room temperature, followed by tetrakis(triphenylphosphine)palladium(0) (0.55 mmol, 0.64 g). The resulting mixture was warmed to reflux and stirred for 18 hours, then cooled to room temperature and subjected to standard aqueous workup to afford the title compound which was used crude in the next step.

Workup

  1. temperatureThe resulting mixture was warmed
  2. temperatureto reflux

Sources & evidence

ORD record
ord-75ea47a9512449939a7d3f0375b27f6f
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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