Acetonitrile → 2-Chloro-1-(3-fluoro-benzyloxy)-4-nitro-benzene

HRID 2093283Notes

Reaction equation

HRID 2093283 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16]Br.C(#N)C.C(=O)([O-])[O-].[K+].[K+]>O>[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH2:16][O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 12074NitrofunginHCID 680073-Fluorobenzyl bromide

Product 1

HCID 70592692-Chloro-1-(3-fluoro-benzyloxy)-4-nitro-benzeneYield 95.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2-chloro-4-nitrophenol (9.02 g, 52 mmol)), 3-fluorobenzyl bromide (9.85 g, 52 mmol) and acetonitrile (90 mL) was combined at room temperature under nitrogen. Potassium carbonate (7.9 g, 57 mmol)) was added and the reaction mixture stirred at 60° C. for 2 hours and then cooled to room temperature. After cooling the reaction mixture was poured into water. The solids were collected by filtration and washed with diethyl ether to afford the desired product (13.98 g, 95% yield). [TLC system=1:1 EtOAc:Hexanes, Rf=0.76]

Workup

  1. customwas combined at room temperature under nitrogen
  2. temperaturecooled to room temperature
  3. temperatureAfter cooling the reaction mixture
  4. filtrationThe solids were collected by filtration
  5. washwashed with diethyl ether

Sources & evidence

ORD record
ord-01e0face01974130b62290932b8cbd2e
Source dataset
uspto-grants-2013_05
Patent number
US08444988B2

Reaction notes

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