Triethylsilane → 4-(4-Bromomethylbenzyl)-nitrobenzene

HRID 1358812Notes

Reaction equation

HRID 1358812 reaction equation
[Br:1][CH2:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=O)=[CH:5][CH:4]=1.FC(F)(F)S(O)(=O)=O.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][CH2:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 12052Triethylsilane2×HCID 62406Trifluoromethanesulfonic acid2×HCID 516892Sodium BicarbonateHCID 143775484-Bromomethyl-4'-nitrobenzophenone

Product 1

HCID 218770124-(4-Bromomethylbenzyl)-nitrobenzeneYield 56.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

4-(4-bromomethylbenzoyl)-nitrobenzene (500 mg) was dissolved in dichloromethane (5 mL) and stirred under argon. A solution of trifluoromethanesulfonic acid (0.27 mL) in dichloromethane (2 mL) was added dropwise, followed by a solution of triethylsilane (0.37 mL) in dichloromethane (2 mL). After 5 minutes, a second portion of trifluoromethanesulfonic acid and triethylsilane (same proportions) was added. The reaction mixture was stirred at room temperature for 3 hours, poured into excess aqueous sodium bicarbonate, and extracted with dichloromethane (3X). The solution containing the crude product was evaporated, chromatographed on silica gel, eluting the product with hexane/ethyl acetate, and evaporated to dryness, to give 4-(4-bromomethylbenzyl)-nitrobenzene (270 mg, 56%).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours
  2. extractionextracted with dichloromethane (3X)
  3. additionThe solution containing the crude product
  4. customwas evaporated
  5. customchromatographed on silica gel
  6. washeluting the product with hexane/ethyl acetate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-9de0010542394cb3a465ad742f372568
Source dataset
uspto-grants-2003_07
Patent number
US06596876B2

Reaction notes

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