Chlorotrimethylsilane → HCID 86632315, compound

HRID 1527893Notes

Reaction equation

HRID 1527893 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10](Br)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Li]CCCC.[CH3:22][Si:23](Cl)([CH3:25])[CH3:24]>C1COCC1>[C:1]([O:5][C:6](=[O:16])[N:7]([C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[C:10]([Si:23]([CH3:25])([CH3:24])[CH3:22])[CH:9]=1)[Si:23]([CH3:25])([CH3:24])[CH3:22])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 58764366tert-Butyl (3-bromo-4-methylphenyl)carbamateHCID 178418339Butyllithium

Product 1

HCID 86632315HCID 86632315, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of tert-butyl(3-bromo-4-methylphenyl)carbamate (2.86 g, 10 mmol) in THF (20 mL) was added n-BuLi (2.5 M in hexanes, 8.8 mL, 22 mmol) at −78° C. and the solution was stirred at this temperature for another 30 min. Trimethylsilyl chloride (2.39 g, 22 mmol) was added at −78° C. and the reaction mixture was then allowed to warm up to r.t. and stirred at r.t. for 1 hr. The reaction was quenched with H2O. EtOAc and more water were added for extraction. The combined organic layer was dried (Na2SO4), filtered, concentrated, and the resulting residue was purified by silica gel flash chromatography (eluted with 20% EtOAc in Hexanes) to give the desired product as a white solid (3.33 g, 95%).

Workup

  1. stirringstirred at r.t. for 1 hr
  2. customThe reaction was quenched with H2O
  3. additionEtOAc and more water were added for extraction
  4. dry with materialThe combined organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe resulting residue was purified by silica gel flash chromatography (eluted with 20% EtOAc in Hexanes)

Sources & evidence

ORD record
ord-e03d95bab53e4b0988aa58b73a028c55
Source dataset
uspto-grants-2015_07
Patent number
US09090561B2

Reaction notes

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