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

HRID 38506

Reaction equation

HRID 38506 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].[OH-].[K+].O.Cl[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[Cl:23]>C(OCC)(=O)C.C1(C)C=CC=CC=1>[Cl:23][C:15]1[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:14]=1[O:6][CH2:5][C:4]1[CH:7]=[CH:8][CH:9]=[C:2]([F:1])[CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 74431,2-Dichloro-4-nitrobenzeneHCID 14797Potassium HydroxideHCID 680083-Fluorobenzylic alcohol

Product 1

HCID 70592692-Chloro-1-(3-fluoro-benzyloxy)-4-nitro-benzeneYield 63%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of 3-fluorobenzyl alcohol (7.88 g, 62.5 mmol), Aliquot 336 (8.08 g, 20.0 mmol), potassium hydroxide (3.51 g, 62.5 mmol) and water (40 mL) were added toluene (80 mL) and 1,2-dichloro-4-nitrobenzene (10.0 g, 52.1 mmol). The mixture was heated to 60° C. overnight with vigorous stirring. The mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate, and the solvent was removed in vacuo. The residue was triturated with hot petroleum ether and tert-butyl methyl ether to yield 9.20 g (63%) of the title compound.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customthe solvent was removed in vacuo
  4. customThe residue was triturated with hot petroleum ether and tert-butyl methyl ether

Sources & evidence

ORD record
ord-69410e23ead34d7c983e71982da85b2a
Source dataset
uspto-grants-2013_09
Patent number
US08524722B2

Linked notes

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