p-Fluoronitrobenzene → HCID 13145675, compound

HRID 2166845Notes

Reaction equation

HRID 2166845 reaction equation
[H-].[Na+].[Cl:3][C:4]1[C:9]([Cl:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:5]=1[OH:13].F[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1>CN(C=O)C>[Cl:10][C:9]1[C:4]([Cl:3])=[C:5]([O:13][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH:6]=[CH:7][C:8]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 24758Sodium hydrideHCID 5130515HCID 5130515, compound

Product 1

HCID 13145675HCID 13145675, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (2.5 g., 0.052 mole of a 50% mineral oil suspension) in 60 ml. of DMF was added portionwise 2,3-dichloro-4-methoxyphenol (9.0 g., 0.047 mole) prepared as described by F. Dallacker and J. Van Wersch, Chem. Ber., 105, 3301 (1972). The mixture was stirred at room temperature under nitrogen for 15 minutes and then p-fluoronitrobenzene was rapidly added. The resulting mixture was heated at 100° for 2.5 hr., cooled to room temperature, and poured into ice water. The precipitate was filtered, washed with methanol and dried to give 13 g. of product, m.p. 165°-166°.

Workup

  1. customprepared
  2. temperatureThe resulting mixture was heated at 100° for 2.5 hr
  3. temperature, cooled to room temperature
  4. filtrationThe precipitate was filtered
  5. washwashed with methanol
  6. customdried
  7. customto give 13 g

Sources & evidence

ORD record
ord-a99e24b048824a2a9b65d1323768300e
Source dataset
uspto-grants-1983_06
Patent number
US04389416

Reaction notes

Loading…