Hydrochloric Acid → 3-Bromo-2,6-diethyl-4-methylaniline

HRID 1649577Notes

Reaction equation

HRID 1649577 reaction equation
Cl.[CH2:2]([C:4]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH2:12][CH3:13])[C:5]=1[NH2:6])[CH3:3].[Br:14]Br>O>[Br:14][C:10]1[C:4]([CH2:2][CH3:3])=[C:5]([C:7]([CH2:12][CH3:13])=[CH:8][C:9]=1[CH3:11])[NH2:6]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 24408BromineHCID 905362,6-Diethyl-p-toluidine

Product 1

HCID 204792043-Bromo-2,6-diethyl-4-methylaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Concentrated HCl (10 ml) is cooled to 5° C. in an ice-water bath and 1.63 g of 2,6-diethyl-4-methylaniline is added dropwise to give a slurry. Bromine (1.59 g) with 10 ml of concentrated HCl is added dropwise over 30 minutes. The reaction is allowed to stir for 3.75 hours and 25 ml of distilled water is added. After cooling for 1.0 hour, the reaction mixture is filtered and washed twice with 25 ml of cold distilled water. After drying under vacuum for about 16 hours, the crude solid (2.3 g) is dissolved in 100 ml of 10% NaOH and extracted with a 150 ml portion and with a 100 ml portion of methylene chloride. After drying over sodium sulfate, the methylene chloride solution is rotary evaporated to 1.9 g of crude product.

Workup

  1. customto give a slurry
  2. temperatureAfter cooling for 1.0 hour
  3. filtrationthe reaction mixture is filtered
  4. washwashed twice with 25 ml
  5. distillationof cold distilled water
  6. customAfter drying under vacuum for about 16 hours
  7. dissolutionthe crude solid (2.3 g) is dissolved in 100 ml of 10% NaOH
  8. extractionextracted with a 150 ml portion and with a 100 ml portion of methylene chloride
  9. dry with materialAfter drying over sodium sulfate
  10. customthe methylene chloride solution is rotary evaporated to 1.9 g of crude product

Sources & evidence

ORD record
ord-e1677bd6edb94f15bc1f391a5d46a132
Source dataset
uspto-grants-1983_11
Patent number
US04418208

Reaction notes

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