Benzyl Bromide → HCID 913402, compound

HRID 1374850Notes

Reaction equation

HRID 1374850 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl.C(OCC)(=O)C>[CH2:16]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 97314-Fluoroaniline

Product 1

HCID 913402HCID 913402, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-fluoroaniline (1.50 g, 13.5 mmol)and triethylamine (2.26 mL, 16.2 mmol) in dichloromethane (7 mL) was cooled to 0° C., and the solution was added dropwise with benzyl bromide (1.61 mL, 13.5 mmol). After stirring at room temperature for 1 hour, the reaction mixture was diluted with ethyl acetate and washed three times with water and then with brine, and dried over Na2SO4. The drying agent was removed by filtration and the filtrate was concentrated, the residue was purified by silica gel chromatography (ethyl acetate/hexane) to obtain the title compound (yield: 46%).

Workup

  1. washwashed three times with water
  2. dry with materialwith brine, and dried over Na2SO4
  3. customThe drying agent was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customthe residue was purified by silica gel chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-cf15c83cb22a40deb7cb91c533131ed7
Source dataset
uspto-grants-2007_01
Patent number
US07166617B2

Reaction notes

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