Water → 4-Bromo-2-ethyl-6-methylaniline

HRID 1353529Notes

Reaction equation

HRID 1353529 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[NH2:10])[CH3:2].O.[Br:12]Br>Cl>[Br:12][C:7]1[CH:6]=[C:5]([CH3:9])[C:4]([NH2:10])=[C:3]([CH2:1][CH3:2])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 324852-Ethyl-6-methylaniline

Product 1

HCID 9607614-Bromo-2-ethyl-6-methylaniline

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-Ethyl-6-methyl-phenylamine (14 mL, 100 mmol) was dissolved in concentrated hydrochloric acid (30 mL) and water (220 mL) and cooled to 0° C. To this was added bromine (5.1 mL, 1 equiv.) dropwise. There was rapid formation of a white precipitate. The precipitate was filtered and washed with diethyl ether. The precipitate was suspended in water and neutralized with aqueous potassium carbonate. An oil formed which was extracted into diethyl ether. The ethereal was dried over potassium carbonate, filtered, and concentrated to give 7.0 g (33%) as a purple oil which was used without purification. Mass spec.: 214.01 (MH)+.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with diethyl ether
  3. customAn oil formed which
  4. extractionwas extracted into diethyl ether
  5. dry with materialThe ethereal was dried over potassium carbonate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give 7.0 g (33%) as a purple oil which
  9. customwas used without purification

Sources & evidence

ORD record
ord-6d52768e0ba34eb6bd225211de50bb73
Source dataset
uspto-grants-2007_05
Patent number
US07220862B2

Reaction notes

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