1-Bromooctane → HCID 20536414, compound

HRID 1156102Notes

Reaction equation

HRID 1156102 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[C:4]([F:13])[CH:3]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[OH-].[K+]>C(O)C.[Cu]>[F:13][C:4]1[CH:3]=[C:2]([NH:1][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH:12]=[CH:11][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

6

Reactant 3

HCID 81401-BromooctaneHCID 14797Potassium HydroxideHCID 10797532Ethyl 4-Amino-2-fluorobenzoate

Product 1

HCID 20536414HCID 20536414, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 702EthanolSolvent

Procedure

A mixture of 33 g of ethyl 4-amino-2-fluorobenzoate, 44 ml of 1-bromooctane and 0.50 g of copper powder is heated on a steam bath for 19 hours. The mixture is chilled, diluted with ethanol, filtered and the solid washed with cold ethanol and with water to give tan crystals. The filtrate is neutralized with 10 N potassium hydroxide, chilled and filtered and the solid washed with water and with ethanol to give tan crystals. The two crops of crystals are combined and recrystallized from ethanol to yield ethyl 2-fluoro-4-(octylamino)benzoate as a white solid.

Workup

  1. temperatureis heated on a steam bath for 19 hours
  2. temperatureThe mixture is chilled
  3. filtrationfiltered
  4. washthe solid washed with cold ethanol and with water
  5. customto give tan crystals
  6. temperaturechilled
  7. filtrationfiltered
  8. washthe solid washed with water and with ethanol
  9. customto give tan crystals
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-ba347b847ec049449b3aa8233952a331
Source dataset
uspto-grants-1982_06
Patent number
US04333940

Reaction notes

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