Benzyl Bromide → HCID 70816196, compound

HRID 1842917Notes

Reaction equation

HRID 1842917 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[F:9].C([O-])([O-])=O.[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC#N>[CH2:16]([N:6]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[C:3]([F:9])[CH:4]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 8218484-Bromo-3-fluoroaniline

Product 1

HCID 70816196HCID 70816196, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of 4-bromo-3-fluoroaniline (10.0 g, 52.6 mmol, 1.0 eq) and K2CO3 (21.7 g, 157.8 mmol, 3.0 eq) in MeCN (10 mL) was added benzyl bromide (19.8 g, 115.8 mmol, 2.2 eq) and the mixture was stirred for 16 h at 80° C. and then filtered through celite pad, and the solvents was evaporated under vacuum and washed with PE (100 mL) to get N,N-dibenzyl-4-bromo-3-fluoroaniline (13.8 g, 55%; TLC system: EtOAc/PE (1:9), Rf: 0.6).

Workup

  1. filtrationfiltered through celite pad
  2. customthe solvents was evaporated under vacuum
  3. washwashed with PE (100 mL)

Sources & evidence

ORD record
ord-8c4865fcc9e448fa8d9057fe038d3737
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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