Triethylsilane → N-[4-(2-Bromoethyl)-2,5-dimethylphenyl]acetamide

HRID 1822903Notes

Reaction equation

HRID 1822903 reaction equation
C([SiH](CC)CC)C.[Br:8][CH2:9][C:10]([C:12]1[C:17]([CH3:18])=[CH:16][C:15]([NH:19][C:20](=[O:22])[CH3:21])=[C:14]([CH3:23])[CH:13]=1)=O>FC(F)(F)C(O)=O>[Br:8][CH2:9][CH2:10][C:12]1[C:17]([CH3:18])=[CH:16][C:15]([NH:19][C:20](=[O:22])[CH3:21])=[C:14]([CH3:23])[CH:13]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 221696594'-(2-Bromoacetyl)-2',5'-dimethylacetanilide

Product 1

HCID 22169691N-[4-(2-Bromoethyl)-2,5-dimethylphenyl]acetamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane 60 mL (375 mmol) was added to trifluoroacetic acid 360 mL and stirred until a homogenous mixture was obtained (15 minutes). This mixture was then added to solid N-[4-(2-bromo-acetyl)-2,5-dimethyl-phenyl]-acetamide 28.88 g (101.64 mmol) in an ice-cooled flask. The flask was capped with a Dryerite-filled tube (as a gas outlet) and the mixture was stirred on ice bath for 1 hour, then at room temperature for 1 day. The reaction mixture was evaporated and the obtained thick residue was suspended in hexane (0.3 L). Water (100 mL) was added and the mixture was stirred and occasionally shaken for about 1 hour. The formed precipitate was collected by filtration, washed repeatedly with plenty of hexane and water, compressed on the frit, dried by air suction, then on high vacuum.

Workup

  1. customwas obtained (15 minutes)
  2. temperaturecooled flask
  3. customThe flask was capped with a Dryerite-filled tube (as a gas outlet)
  4. stirringthe mixture was stirred on ice bath for 1 hour
  5. customThe reaction mixture was evaporated
  6. additionWater (100 mL) was added
  7. stirringthe mixture was stirred
  8. stirringoccasionally shaken for about 1 hour
  9. filtrationThe formed precipitate was collected by filtration
  10. washwashed repeatedly with plenty of hexane and water
  11. customdried by air suction

Sources & evidence

ORD record
ord-b40204a8d888418591101ed62c5ccb30
Source dataset
uspto-grants-2006_05
Patent number
US07037909B2

Reaction notes

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