2,6-Dimethylaniline → 4-Bromo-2,6-xylidine

HRID 1446365Notes

Reaction equation

HRID 1446365 reaction equation
[Br:1]Br.[CH3:3][C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:5]=1[NH2:6]>C(O)(=O)C>[Br:1][C:9]1[CH:8]=[C:7]([CH3:11])[C:5]([NH2:6])=[C:4]([CH3:3])[CH:10]=1

Participants

4

Reactant 2

HCID 68962,6-DimethylanilineHCID 24408Bromine

Product 1

HCID 905494-Bromo-2,6-xylidine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

21.3 ml (66.1 g, 0.413 mol) of bromine were added dropwise, while vigorously stirring, over ca. 20 minutes to a solution of 50.0 g (0.413 mol) of 2,6-dimethylaniline in 1200 cm3 of glacial acetic acid. This mixture was stirred for 2 hours at 40° C. The precipitate formed was filtered off, washed with 50 ml of acetic acid, and dried in air. Then, this white solid was added to a solution of 100 g of sodium hydroxide in 600 ml of water. This mixture was stirred for 30 minutes. The crude product was extracted with 3×100 ml of dichloromethane. The combined organic fractions were dried over Na2SO4 and evaporated to dryness. Fractional distillation gave a yellow liquid, bp 82-85° C./1 mm Hg. Yield 61.7 g (75%).

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered off
  3. washwashed with 50 ml of acetic acid
  4. customdried in air
  5. additionThen, this white solid was added to a solution of 100 g of sodium hydroxide in 600 ml of water
  6. stirringThis mixture was stirred for 30 minutes
  7. extractionThe crude product was extracted with 3×100 ml of dichloromethane
  8. dry with materialThe combined organic fractions were dried over Na2SO4
  9. customevaporated to dryness
  10. distillationFractional distillation
  11. customgave a yellow liquid, bp 82-85° C./1 mm Hg

Sources & evidence

ORD record
ord-20acdf8468ae47c0a99d4b1ce1ab6e1e
Source dataset
uspto-grants-2010_02
Patent number
US07667064B2

Reaction notes

Loading…