Sodium Hydroxide → N-(2-bromoethyl)-4-fluoro-2-nitrobenzamide

HRID 437648Notes

Reaction equation

HRID 437648 reaction equation
Br.[Br:2][CH2:3][CH2:4][NH2:5].[F:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[C:9]([N+:16]([O-:18])=[O:17])[CH:8]=1.[OH-].[Na+]>O.C1C=CC=CC=1>[Br:2][CH2:3][CH2:4][NH:5][C:11](=[O:12])[C:10]1[CH:14]=[CH:15][C:7]([F:6])=[CH:8][C:9]=1[N+:16]([O-:18])=[O:17]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 27742172-Bromoethylamine hydrobromideHCID 133524084-Fluoro-2-nitrobenzoyl chloride

Product 1

HCID 21428900N-(2-bromoethyl)-4-fluoro-2-nitrobenzamideYield 93.6%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent2×

Procedure

To a stirred and cooled mixture of 32 parts of 2-bromoethanamine hydrobromide in 150 parts of water is added a solution of 23.5 parts of 4-fluoro-2-nitrobenzoyl chloride in 54 parts of benzene. While cooling to 0°-5° C and while stirring vigourously, there is added dropwise a solution of 13 parts of sodium hydroxide in 200 parts of water (exothermic reaction). Upon completion, stirring is continued for 2 hours at 0°-10° C. The precipitated product is filtered off, washed with water and dried, yielding 30 parts (93.6%) of N-(2-bromoethyl)-4-fluoro-2-nitrobenzamide.

Workup

  1. temperaturecooled
  2. temperatureWhile cooling to 0°-5° C
  3. stirringwhile stirring vigourously
  4. stirringUpon completion, stirring
  5. filtrationThe precipitated product is filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-97819f0b17c84c1e9e7aa2058d99ab28
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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