4-Fluorobenzyl chloride → 2-Fluoro-4-(4-fluoro-benzyloxy)-nitrobenzene

HRID 2225392Notes

Reaction equation

HRID 2225392 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[F:1][C:2]1[CH:3]=[C:4]([O:11][CH2:19][C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 96024-Fluorobenzyl chlorideHCID 11430Potassium CarbonateHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 221379402-Fluoro-4-(4-fluoro-benzyloxy)-nitrobenzeneYield 18.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
70 °C

Procedure

A stirred mixture of 10.0 g (0.063 mole) of 3-fluoro-4-nitrophenol, 17.0 g (0.090 mole) of 4-fluorophenylmethyl chloride, and 12.42 g (0.090 mole) of anhydrous potassium carbonate in 80 mL of methyl ethyl ketone was heated at 70° C. for approximately 17 hours. The reaction mixture was then cooled and filtered and the filtrate evaporated under reduced pressure, leaving 3.10 g of 4-fluorophenylmethyl 3-fluoro-4-nitrophenyl ether as a solid; m.p. 90°-91° C.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. filtrationfiltered
  3. customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-51b972a351a5481fa043bd6406a178b5
Source dataset
uspto-grants-1994_09
Patent number
US05344812

Reaction notes

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