2-Chlorophenol → HCID 3432930, compound

HRID 1464444Notes

Reaction equation

HRID 1464444 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19]>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 72452-ChlorophenolHCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 3432930HCID 3432930, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Sodium hydride (1.00 g) was added in portions to a solution of 2-chlorophenol (5.00 g) in N,N-dimethylformamide (100 mL) under nitrogen. To the resulting solution was added 2-fluoro-1-nitrobenzene (5.00 g). The mixture was heated at 65° C. overnight, and then was evaporated under vacuum. The residue was partitioned between chloroform and 1 N NaOH, and the layers were separated. The aqueous layer was extracted once more with chloroform, and the combined chloroform layers were washed with water and brine, dried over magnesium sulfate, and evaporated under vacuum to a yellow oil. The oil was crystallized from ethyl ether/hexane at -78° C. to yield the title compound as a light yellow solid. Mp: 48°-49° C.

Workup

  1. customwas evaporated under vacuum
  2. customThe residue was partitioned between chloroform and 1 N NaOH
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted once more with chloroform
  5. washthe combined chloroform layers were washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under vacuum to a yellow oil
  8. customThe oil was crystallized from ethyl ether/hexane at -78° C.

Sources & evidence

ORD record
ord-c7d56218c9d04584ad870404ed4d4f20
Source dataset
uspto-grants-1994_04
Patent number
US05304644

Reaction notes

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