1-Bromo-3-chloropropane → HCID 19597310, compound

HRID 611851Notes

Reaction equation

HRID 611851 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[C:7]([C:12](=O)[CH3:13])[CH:8]=[CH:9][C:10]=1[OH:11])(=[O:3])[CH3:2].C([O-])([O-])=[O:16].[K+].[K+].[Cl:21][CH2:22][CH2:23][CH2:24]Br>CC(C)=O>[C:1]([NH:4][C:5]1[CH:6]=[C:7]([CH2:12][CH:13]=[O:16])[CH:8]=[CH:9][C:10]=1[O:11][CH2:24][CH2:23][CH2:22][Cl:21])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 283886N-(5-Acetyl-2-hydroxyphenyl)ethanimidic acid

Product 1

HCID 19597310HCID 19597310, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A stirred mixture of 1-[3-acetylamino-4-hydroxyphenyl] ethanone (7.7 g, 40 mmol), K2CO3 (5.7 g), 3-chloro-1-bromopropane (8.9 g, 56 mmol) and acetone (100 ml) was refluxed for 16 hours. The reaction was allowed to cool to ambient temperature and filtered. Concentration of the filtrate yielded 8.5 g of a white solid. The solid was recrystallized from toluene and then from ethanol to afford 6.5 g of an off-white solid. A 3.3 g sample of this material was flash chromatographed on silica gel with ethyl acetate as eluent. Concentration of the appropriate fractions afforded 2.8 g of a solid. The solid was recrystallized from toluene and then from ethanol-water to yield 2.2 g (51%) of a solid, m.p.=124-126° C.

Workup

  1. temperaturewas refluxed for 16 hours
  2. filtrationfiltered

Sources & evidence

ORD record
ord-bb8cb8387e694999aba92f3f3d60fbb2
Source dataset
uspto-grants-1999_12
Patent number
US06001834

Reaction notes

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