Benzyl Bromide → HCID 11143579, compound

HRID 2083854Notes

Reaction equation

HRID 2083854 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.[CH2:11](Br)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:11]([N:6]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]1[C:7]([F:9])=[CH:8][C:2]([Br:1])=[CH:3][C:4]=1[F:10])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 6101914-Bromo-2,6-difluoroaniline

Product 1

HCID 11143579HCID 11143579, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 416 g of 4-bromo-2,6-difluoroaniline, 752 g of benzyl bromide and 608 g of potassium carbonate in 2 l of acetonitrile is refluxed for 48 hours. The mixture is subsequently evaporated in a rotary evaporator, the residue is dissolved in toluene and extracted with hydrochloric acid (10%), the toluene phase is evaporated in a rotary evaporator, and the product is stirred into heptane and stirred with silica gel for about 4.5 hours, filtered with suction and evaporated in a rotary evaporator, giving dibenzyl(4-bromo-2,6-difluorophenyl)amine, yield 85.6%.

Workup

  1. temperatureis refluxed for 48 hours
  2. customThe mixture is subsequently evaporated in a rotary evaporator
  3. dissolutionthe residue is dissolved in toluene
  4. extractionextracted with hydrochloric acid (10%)
  5. customthe toluene phase is evaporated in a rotary evaporator
  6. stirringstirred with silica gel for about 4.5 hours
  7. filtrationfiltered with suction
  8. customevaporated in a rotary evaporator

Sources & evidence

ORD record
ord-51c4fc4537f64441b3ecb7489f8b3016
Source dataset
uspto-grants-2004_04
Patent number
US06716491B2

Reaction notes

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