2-(Bromomethyl)-4-fluoro-1-nitrobenzene → N-(5-fluoro-2-nitrophenyl)methyl-phthalimide

HRID 1030529Notes

Reaction equation

HRID 1030529 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH:9]=1)[CH2:7]Br.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.[K]>CN(C)C=O.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-:12])=[O:11])=[C:6]([CH2:7][N:17]2[C:16](=[O:18])[C:15]3=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]3[C:13]2=[O:23])[CH:9]=1

Participants

5

Reactant 2

HCID 105616432-(Bromomethyl)-4-fluoro-1-nitrobenzeneHCID 24194345Phthalimide potassium salt

Product 1

HCID 19820552N-(5-fluoro-2-nitrophenyl)methyl-phthalimide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 5-fluoro-2-nitro-benzylbromide (6.2 g) in dimethylformamide (20 ml) was dropped into a stirred suspension of potassium phthalimide (4.9 g) in the same solvent (40 ml). The mixture was heated under stirring to 90° C. for 2 hours, then cooled and diluted with water. The title compound (7.2 g) was recovered by filtration. M.p. 198°-200° C.

Workup

  1. temperatureThe mixture was heated
  2. temperaturecooled
  3. filtrationThe title compound (7.2 g) was recovered by filtration

Sources & evidence

ORD record
ord-bab01ec25e174a5e9e8ea8ea18f37e6f
Source dataset
uspto-grants-1992_04
Patent number
US05106851

Reaction notes

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